EU/US Properties Organoleptics Cosmetics Suppliers Safety Safety in use Safety references References Other Blenders Uses Occurrence Synonyms Articles Notes
 

pulegone
p-menth-4(8)-en-3-one

Supplier Sponsors

Fragrance Demo Formulas
Name:5-methyl-2-propan-2-ylidenecyclohexan-1-one
CAS Number: 15932-80-6Picture of molecule3D/inchi
Other(deleted CASRN):3285-04-9
ECHA EINECS - REACH Pre-Reg:240-070-1
FDA UNII: Search
Nikkaji Web:J112.664D
XlogP3-AA:2.80 (est)
Molecular Weight:152.23672000
Formula:C10 H16 O
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:fragrance agents
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
Google Books:Search
Google Scholar: with word "volatile"Search
Google Scholar: with word "flavor"Search
Google Scholar: with word "odor"Search
Perfumer and Flavorist:Search
Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
FEMA Number:2963-VOID pulegone
FDA:No longer provide for the use of these seven synthetic flavoring substances
 
Physical Properties:
Appearance:colorless clear liquid (est)
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Specific Gravity:0.92700 to 0.93900 @ 25.00 °C.
Pounds per Gallon - (est).: 7.714 to 7.813
Refractive Index:1.48300 to 1.49100 @ 20.00 °C.
Boiling Point: 221.00 to 223.00 °C. @ 760.00 mm Hg
Vapor Pressure:0.093000 mmHg @ 25.00 °C. (est)
Flash Point: 198.00 °F. TCC ( 92.22 °C. )
logP (o/w): 1.439 (est)
Soluble in:
 alcohol
 water, 173.7 mg/L @ 25 °C (est)
Insoluble in:
 water
 
Organoleptic Properties:
Odor Description:minty
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
Aurochemicals
PULEGONE, Natural
Bontoux
PULEGONE NATURAL ISOLATE
Charabot
Pulegone nat
100% Pure & Natural, Kosher
Odor: Aromatic, minty, green, herbaceous, bitter
Robertet
Pulegone nat
100% Pure & Natural, Kosher
Odor: Aromatic, minty, green, herbaceous, bitter
Seasons and Harvest / Crop calendar
Chemical Sources Association
Need This Item for Flavor/Food?: You can contact the Chemical Sources Association
 
Safety Information:
European information :
Most important hazard(s):
Xn - Harmful.
R 22 - Harmful if swallowed.
R 36/38 - Irritating to skin and eyes.
S 02 - Keep out of the reach of children.
S 20/21 - When using do not eat, drink or smoke.
S 24/25 - Avoid contact with skin and eyes.
S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S 37/39 - Wear suitable gloves and eye/face protection.
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
oral-rat LD50 470 mg/kg
Food and Cosmetics Toxicology. Vol. 16, Pg. 867, 1978.

intraperitoneal-mouse LD50 150 mg/kg
National Technical Information Service. Vol. AD691-490

Dermal Toxicity:
skin-rabbit LD50 3090 mg/kg
Food and Cosmetics Toxicology. Vol. 16, Pg. 867, 1978.

subcutaneous-mouse LD50 1709 mg/kg
BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Food and Cosmetics Toxicology. Vol. 16, Pg. 867, 1978.

Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
fragrance agents
RIFM Fragrance Material Safety Assessment: Search
IFRA Code of Practice Notification of the 49th Amendment to the IFRA Code of Practice
 
Use levels for FEMA GRAS flavoring substances on which the FEMA Expert Panel based its judgments that the substances are generally recognized as safe (GRAS).
The Expert Panel also publishes separate extensive reviews of scientific information on all FEMA GRAS flavoring substances and can be found at FEMA Flavor Ingredient Library
publication number: 3
Click here to view publication 3
 average usual ppmaverage maximum ppm
baked goods: 24.0000025.00000
beverages(nonalcoholic): 5.000008.00000
beverages(alcoholic): --
breakfast cereal: --
cheese: --
chewing gum: --
condiments / relishes: --
confectionery froastings: --
egg products: --
fats / oils: --
fish products: --
frozen dairy: 5.0000032.00000
fruit ices: 5.0000032.00000
gelatins / puddings: --
granulated sugar: --
gravies: --
hard candy: -17.00000
imitation dairy: --
instant coffee / tea: --
jams / jellies: --
meat products: --
milk products: --
nut products: --
other grains: --
poultry: --
processed fruits: --
processed vegetables: --
reconstituted vegetables: --
seasonings / flavors: --
snack foods: --
soft candy: --
soups: --
sugar substitutes: --
sweet sauces: --
 
Safety References:
European Food Safety Authority (EFSA) reference(s):

Flavouring Group Evaluation 57 (FGE.57)[1]: Consideration of two structurally related pulegone metabolites and one ester thereof evaluated by JECFA (55th meeting)
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 213, Revision 2 (FGE.213Rev2): Consideration of genotoxic potential for a,ß-unsaturated alicyclic ketones and precursors from chemical subgroup 2.7 of FGE.19
View page or View pdf

EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):15932-80-6
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :6988
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
5-methyl-2-propan-2-ylidenecyclohexan-1-one
Chemidplus:0015932806
RTECS:OT0260000 for cas# 15932-80-6
 
References:
 5-methyl-2-propan-2-ylidenecyclohexan-1-one
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:15932-80-6
Pubchem (cid):6988
Pubchem (sid):134972995
Pherobase:View
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
CHEMBL:View
HMDB (The Human Metabolome Database):Search
FooDB:FDB014299
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
For Odor
No odor group found for these
cyclopentanone
FL/FR
laevo-mono
menthyl glutarate
FL/FR
laevo-
menthyl methyl ether
FL/FR
pinocarvone
FL/FR
aldehydic
aldehydic
iso
butyraldehyde
FL/FR
anisic
estragole
FL/FR
balsamic
iso
bornyl formate
FL/FR
camphoreous
dextro-
camphor
FL/FR
camphor tree bark oil
FL/FR
herbal ethanone
FR
thujyl alcohol
FL/FR
citrus
ocimene quintoxide
FL/FR
earthy
3-
octanol
FL/FR
patchouli cyclohexanol
FR
floral
citronellal diisotridecyl acetal
FR
cyclohexyl ethyl acetate
FL/FR
cyclohexyl propanol
FR
2-
decalinol
FR
dihydrocarvyl acetate
FL/FR
2',4'-
dimethyl acetophenone
FL/FR
earthy indane
FR
floral methanol
FR
geranium oil china
FL/FR
menthadienyl formate
FR
muguet butanol
FR
ylang ylang flower oil
FL/FR
ylang ylang flower oil CO2 extract
FL/FR
ylang ylang flower oil I
FL/FR
ylang ylang flower oil II
FL/FR
ylang ylang flower oil III
FL/FR
fruity
3-
benzyl-4-heptanone
FL/FR
2-
cyclopentyl cyclopentanone
FL/FR
lilac lactone
FL/FR
green
geranium absolute
FL/FR
thiogeraniol
FL/FR
herbal
artemisyl ketone
FL/FR
barosma betulina leaf oil
FL/FR
1,4-
cineole
FL/FR
costmary oil (chrysanthemum balsamita)
FR
dehydroxylinalool oxide
FL/FR
iso
dihydrolavandulol
FR
(Z)-iso
dihydrolavandulyl acetate
FR
herbal undecanol
FR
hyssop oil
FL/FR
para-
menthane-3,8-diol
FL/FR
myrtenol
FL/FR
3-
octyl acetate
FL/FR
perillaldehyde
FL/FR
laevo-
perillaldehyde
FL/FR
pine hexanol
FR
D-(+)-alpha-
pinene
FL/FR
piperitone
FL/FR
rosemary absolute
FL/FR
rosemary oil morocco
FL/FR
sabinene hydrate
FL/FR
common
tansy flower oil
FR
common
tansy flower oil dutch
FR
viridiflorol
FL/FR
licorice
sweet
basil oleoresin
FL/FR
mentholic
cornmint oil
FL/FR
cornmint oil india
FL/FR
cornmint oil terpeneless
FL/FR
(±)-
menthol
FL/FR
laevo-
menthol
FL/FR
dextro-neo
menthol
FL/FR
dextro,laevo-
menthol
FL/FR
(±)-iso
menthone
FL/FR
laevo-
menthyl acetate
FL/FR
menthyl acetate
FL/FR
menthyl acetate racemic
FL/FR
peppermint cyclohexanone
FL/FR
dextro-
piperitone
FL/FR
iso
pulegyl acetate
FL/FR
minty
agathosma crenulata leaf oil
FL/FR
laevo-
carveol
FL/FR
carvone
FL/FR
laevo-
carvone
FL/FR
cis-
carvone-5,6-oxide
FL/FR
carvyl propionate
FL/FR
cyclohexanone
FR
dihydrocarveol
FL/FR
diosphenol
FL/FR
ethyl salicylate
FL/FR
bitter
fennel seed oil
FR
dextro-2,8-para-
menthadien-1-ol
FL/FR
trans-para-2,8-1-
menthadienol
FL/FR
trans-para-
menthan-2-one
FL/FR
homo
menthol
FL/FR
(-)-
menthone
FL/FR
(±)-
menthone
FL/FR
menthoxypropane diol
FL/FR
homo
menthyl acetate
FL/FR
2-
methyl cyclohexanone
FL/FR
methyl salicylate
FL/FR
pennyroyal oil
FL/FR
pennyroyal oil spain
FL/FR
pennyroyal oil uruguay
FL/FR
peppermint oil CO2 extract
FL/FR
peppermint oil idaho
FL/FR
peppermint oil russia
FL/FR
peppermint oil terpeneless
FL/FR
beta-
phellandrene
FL/FR
piperitenone
FL/FR
laevo-
piperitone
FL/FR
iso
propyl tiglate
FL/FR
(-)-iso
pulegol
FL/FR
iso
pulegyl formate
FL/FR
spearmint absolute
FL/FR
spearmint oil america
FL/FR
spearmint oil terpeneless
FL/FR
tetrahydrocarvone
FL/FR
vanillin menthoxypropane diol acetal
FL/FR
wintergreen oil
FL/FR
WS-23
FL/FR
spicy
N,N-
diethyl octanamide
FR
laevo-
verbenone
FL/FR
sulfurous
buchu mercaptan
FL/FR
grapefruit menthane
FL/FR
thujonic
armoise oil
FR
common
tansy oil canada
FR
tropical
beta-
cyclocitral
FL/FR
woody
para-tert-
butyl cyclohexanone
FR
patchouli ethanol
FR
patchouli hexanol
FR
cis-2-
pinanol
FR
For Flavor
No flavor group found for these
artemisyl ketone
FL/FR
carvone
FL/FR
cyclopentanone
FL/FR
2-
cyclopentyl cyclopentanone
FL/FR
2',4'-
dimethyl acetophenone
FL/FR
(±)-N,N-
dimethyl menthyl succinamide
FL
iso
heptyl acetate
FL
lilac lactone
FL/FR
limonen-10-yl acetate
FL
dextro-2,8-para-
menthadien-1-ol
FL/FR
cis+trans-para-1(7)8-
menthadien-2-yl acetate
FL
trans-para-2,8-1-
menthadienol
FL/FR
para-
menthane-3,8-diol
FL/FR
3-laevo-
menthoxy-2-methyl propane-1,2-diol
FL
menthyl acetate racemic
FL/FR
laevo-mono
menthyl glutarate
FL/FR
laevo-
menthyl methyl ether
FL/FR
menthyl propylene glycol carbonate
FL
2-
methyl cyclohexanone
FL/FR
beta-
phellandrene
FL/FR
(Z,Z)-
photocitral A
FL
D-(+)-alpha-
pinene
FL/FR
pinocarvone
FL/FR
piperitenone
FL/FR
piperitenone oxide
FL
iso
pulegyl formate
FL/FR
vanillin menthoxypropane diol acetal
FL/FR
laevo-
verbenone
FL/FR
viridiflorol
FL/FR
menthyl methyl lactate
FL
thujyl alcohol
FL/FR
aldehydic
aldehydic
iso
butyraldehyde
FL/FR
alliaceous
benzyl mercaptan
FL
aromatic
laevo-
perillaldehyde
FL/FR
camphoreous
camphor tree bark oil
FL/FR
coffee
2-iso
propyl pyrazine
FL
cooling
1,4-
cineole
FL/FR
laevo-
menthol
FL/FR
dextro,laevo-
menthol
FL/FR
menthoxypropane diol
FL/FR
homo
menthyl acetate
FL/FR
menthyl acetate
FL/FR
sabinene hydrate
FL/FR
WS-5
FL
floral
dihydrocarvyl acetate
FL/FR
geranium oil china
FL/FR
ylang ylang flower oil
FL/FR
ylang ylang flower oil CO2 extract
FL/FR
ylang ylang flower oil I
FL/FR
ylang ylang flower oil II
FL/FR
ylang ylang flower oil III
FL/FR
fruity
3-
benzyl-4-heptanone
FL/FR
green
cyclohexyl ethyl acetate
FL/FR
dihydrocarveol
FL/FR
geranium absolute
FL/FR
ocimene quintoxide
FL/FR
3-
octyl acetate
FL/FR
iso
propyl tiglate
FL/FR
thiogeraniol
FL/FR
herbal
2-
acetoxy-1,8-cineole
FL
barosma betulina leaf oil
FL/FR
hyssop oil
FL/FR
rosemary absolute
FL/FR
rosemary oil morocco
FL/FR
licorice
sweet
basil oleoresin
FL/FR
estragole
FL/FR
meaty
2-
methyl 3-(methyl thio) furan
FL
medicinal
dextro-
camphor
FL/FR
mentholic
cornmint oil
FL/FR
cornmint oil terpeneless
FL/FR
(±)-
menthol
FL/FR
dextro-neo
menthol
FL/FR
peppermint cyclohexanone
FL/FR
minty
agathosma crenulata leaf oil
FL/FR
laevo-
carveol
FL/FR
laevo-
carvone
FL/FR
cis-
carvone-5,6-oxide
FL/FR
carvyl propionate
FL/FR
cornmint oil india
FL/FR
diosphenol
FL/FR
ethyl salicylate
FL/FR
trans-para-
menthan-2-one
FL/FR
homo
menthol
FL/FR
(±)-
menthone
FL/FR
(±)-iso
menthone
FL/FR
(-)-
menthone
FL/FR
laevo-
menthyl acetate
FL/FR
methyl salicylate
FL/FR
myrtenol
FL/FR
pennyroyal oil
FL/FR
pennyroyal oil spain
FL/FR
pennyroyal oil uruguay
FL/FR
peppermint oil CO2 extract
FL/FR
peppermint oil idaho
FL/FR
peppermint oil russia
FL/FR
peppermint oil terpeneless
FL/FR
laevo-
piperitone
FL/FR
piperitone
FL/FR
dextro-
piperitone
FL/FR
(-)-iso
pulegol
FL/FR
spearmint absolute
FL/FR
spearmint oil america
FL/FR
spearmint oil terpeneless
FL/FR
tetrahydrocarvone
FL/FR
wintergreen oil
FL/FR
WS-23
FL/FR
musty
3-
octanol
FL/FR
spicy
4-
methyl biphenyl
FL
perillaldehyde
FL/FR
sulfurous
buchu mercaptan
FL/FR
grapefruit menthane
FL/FR
tropical
beta-
cyclocitral
FL/FR
woody
iso
bornyl formate
FL/FR
dehydroxylinalool oxide
FL/FR
iso
pulegyl acetate
FL/FR
 
Potential Uses:
FRmint
 
Occurrence (nature, food, other):note
 cornmint leaf
Search Trop Picture
 cornmint plant
Search Trop Picture
 peppermint leaf
Search Trop Picture
 spearmint leaf
Search Trop Picture
 spearmint oil
Search Trop Picture
 st. johnswort spotted
Search Trop Picture
 water mint leaf
Search Trop Picture
 ziziphora tenuior
Search Trop Picture
 
Synonyms:
D-p-menth-4(8)-en-3-one
dextro-para-menth-4(8)-en-3-one
p-menth-4(8)-en-3-one
para-menth-4(8)-en-3-one
5-methyl-2-propan-2-ylidenecyclohexan-1-one
(±)-pulegone
 pulegone nat ex pennyroyal
 pulegone natural isolate
 

Articles:

PubMed:Chemical composition of essential oils of Grindelia squarrosa and G. hirsutula.
PubMed:The aversive, anxiolytic-like, and verapamil-sensitive psychostimulant effects of pulegone.
PubMed:An enantiospecific synthesis of jiadifenolide.
PubMed:Development of a Validated HPLC/Photodiode Array Method for the Determination of Isomenthone in the Aerial Parts of Ziziphora tenuior L.
PubMed:Antimicrobial activity against beneficial microorganisms and chemical composition of essential oil of Mentha suaveolens ssp. insularis grown in Sardinia.
PubMed:Systematic approach to conformational sampling for assigning absolute configuration using vibrational circular dichroism.
PubMed:Divergent total synthesis of the Lycopodium alkaloids huperzine A, huperzine B, and huperzine U.
PubMed:Development of a rapid resolution liquid chromatography-diode array detector method for the determination of three compounds in Ziziphora clinopodioides Lam from different origins of Xinjiang.
PubMed:Nematicidal activity of mint aqueous extracts against the root-knot nematode Meloidogyne incognita.
PubMed:[Study on effect and mechanism of volatile oil of schizonepetae herba and its essential components against influenza virus].
PubMed:Individual and joint activity of terpenoids, isolated from Calamintha nepeta extract, on Arabidopsis thaliana.
PubMed:Chemical composition and nematicidal activity of essential oil of Agastache rugosa against Meloidogyne incognita.
PubMed:Anti-Candida zeylanoides activity of some Iranian plants used in traditional medicine.
PubMed:Chemical diversity among the essential oils of wild populations of Stachys lavandulifolia VAHL (Lamiaceae) from Iran.
PubMed:[Stable life predection for Mentha haplocalyx by initial average rate stability test].
PubMed:[Determination of effective time of Schizonepeta tenuifalia pieces by classical constant temperature acceleration experiment].
PubMed:Inhibition by menthol and its related chemicals of compound action potentials in frog sciatic nerves.
PubMed:Structural relationships and vasorelaxant activity of monoterpenes.
PubMed:A near fatal case of high dose peppermint oil ingestion- Lessons learnt.
PubMed:Retention of aroma compounds from Mentha piperita essential oil by cyclodextrins and crosslinked cyclodextrin polymers.
PubMed:Essential oils of Micromeria dalmatica Benth., a Balkan endemic species of section Pseudomelissa.
PubMed:Synergistic combinations of high hydrostatic pressure and essential oils or their constituents and their use in preservation of fruit juices.
PubMed:Phytotoxic activity of foliar volatiles and essential oils of Calamintha nepeta (L.) Savi.
PubMed:Relaxant effects of the essential oil of Mentha pulegium L. in rat isolated trachea and urinary bladder.
PubMed:Characterization of rat liver proteins adducted by reactive metabolites of menthofuran.
PubMed:Essential oils and their compositions as spatial repellents for pestiferous social wasps.
PubMed:Chemical fingerprinting by RP-RRLC-DAD and principal component analysis of Ziziphora clinopodioides from different locations.
PubMed:Synthesis of (R)-(+)-4-methylcyclohex-2-ene-1-one.
PubMed:Antioxidant properties and essential oil composition of Calamintha grandiflora L.
PubMed:In vitro production of M. × piperita not containing pulegone and menthofuran.
PubMed:An efficient total synthesis of (-)-huperzine A.
PubMed:The constituents of essential oil: antimicrobial and antioxidant activity of Micromeria congesta Boiss. & Hausskn. ex Boiss. from East Anatolia.
PubMed:Essential oil composition and antimicrobial activity of wild and cultivated mint timija (Mentha suaveolens subsp. timija (Briq.) Harley), an endemic and threatened medicinal species in Morocco.
PubMed:Essential-oil diversity of three Calamintha species from Greece.
PubMed:Volatile secondary metabolites of Micromeria dalmatica Benth. (Lamiaceae): biosynthetical and chemotaxonomical aspects.
PubMed:Lack of cytotoxic and genotoxic effects of Minthostachys verticillata essential oil: studies in vitro and in vivo.
PubMed:Microarray analysis of the gene expression profile of HMC-1 mast cells following Schizonepeta tenuifolia Briquet treatment.
PubMed:Constituents and biological activity of the essential oil and the aqueous extract of Micromeria fruticosa (L.) Druce subsp. serpyllifolia.
PubMed:Allelopathic potential of Artemisia arborescens: isolation, identification and quantification of phytotoxic compounds through fractionation-guided bioassays.
PubMed:The synergistic effects of insecticidal essential oils and piperonyl butoxide on biotransformational enzyme activities in Aedes aegypti (Diptera: Culicidae).
PubMed:Intraspecific variability of the essential oil of Calamintha nepeta subsp. nepeta from Southern Italy (Apulia).
PubMed:Mode of action of pulegone on the urinary bladder of F344 rats.
PubMed:Assessing the effects of three potential chemical repellents to prevent bird damage to corn seeds and seedlings.
PubMed:GC-MS analysis of Ziziphora clinopodioides essential oil from North Xinjiang, China.
PubMed:Chemical and morphological diversity in wild populations of Mentha longifolia in Israel.
PubMed:Plant terpenoids: acute toxicities and effects on flight motor activity and wing beat frequency in the blow fly Phaenicia sericata.
PubMed:Chemical composition and antibacterial activity of the essential oil from Mentha requienii Bentham.
PubMed:Designer repellents: combining olfactory, visual or taste cues with a secondary repellent to deter free-ranging house sparrows from feeding.
PubMed:Volatile constituents of two Hypericum species from Tunisia.
PubMed:Mentha longifolia in vitro cultures as safe source of flavouring ingredients.
PubMed:Molecular response of Musca domestica L. to Mintostachys verticillata essential oil, (4R)+-pulegone and menthone.
PubMed:Quantitative comparative analysis of the bio-active and toxic constituents of leaves and spikes of Schizonepeta tenuifolia at different harvesting times.
PubMed:Synthesis of the reported structure of trans-africanan-1α-ol.
PubMed:R(+)-pulegone impairs Ca²+ homeostasis and causes negative inotropism in mammalian myocardium.
PubMed:Improving peppermint essential oil yield and composition by metabolic engineering.
PubMed:Pharmacological activity of (R)-(+)-pulegone, a chemical constituent of essential oils.
PubMed:Anti-quorum sensing activity of essential oils from Colombian plants.
PubMed:Toxicology and carcinogenesis studies of pulegone (CAS No. 89-82-7) in F344/N rats and B6C3F1 mice (gavage studies).
PubMed:A solid-phase microextraction GC/MS/MS method for rapid quantitative analysis of food and beverages for the presence of legally restricted biologically active flavorings.
PubMed:Antimicrobial activity of Hedeoma drummondii against opportunistic pathogens.
PubMed:Inhibition of aflatoxin production and growth of Aspergillus parasiticus by Cuminum cyminum, Ziziphora clinopodioides, and Nigella sativa essential oils.
PubMed:Volatile organic compounds from rhizobacteria increase biosynthesis of essential oils and growth parameters in peppermint (Mentha piperita).
PubMed:Chemical composition and antimicrobial activities of the essential oils from Ocimum selloi and Hesperozygis myrtoides.
PubMed:Classification of Greek Mentha pulegium L. (Pennyroyal) samples, according to geographical location by Fourier transform infrared spectroscopy.
PubMed:Chemical diversity of Ziziphora clinopodioides: composition of the essential oil of Z. clinopodioides from Tajikistan.
PubMed:Monoterpenes isolated from Minthostachys verticillata (Griseb.) Epling essential oil modulates immediate-type hypersensitivity responses in vitro and in vivo.
PubMed:Profiling the reactive metabolites of xenobiotics using metabolomic technologies.
PubMed:Herbal bioactivation, molecular targets and the toxicity relevance.
PubMed:Strigolactone analogs derived from ketones using a working model for germination stimulants as a blueprint.
PubMed:Fungicidal properties of the essential oil of Hesperozygis marifolia on Aspergillus flavus link.
PubMed:Toxicity of Schizonpeta multifida essential oil and its constituent compounds towards two grain storage insects.
PubMed:Comparative toxicity of oxygenated monoterpenoids in experimental hydroalcoholic lotions to permethrin-resistant adult head lice.
PubMed:Plant volatiles providing additional evidences to the occurence of a wild-growing population of Calamintha vardarensis (Greuter et Burdet) Šilić outside of its natural habitat.
PubMed:Chemical composition and biological activities of Calamintha officinalis Moench essential oil.
PubMed:D-Isomer of gly-tyr-pro-cys-pro-his-pro peptide: a novel and sensitive in vitro trapping agent to detect reactive metabolites by electrospray mass spectrometry.
PubMed:Chemical composition and biological assays of essential oils of Calamintha nepeta (L.) Savi subsp. nepeta (Lamiaceae).
PubMed:Total synthesis of (+)-nankakurines A and B and (±)-5-epi-nankakurine A.
PubMed:IR-Raman-VCD study of R-(+)-pulegone: influence of the solvent.
PubMed:Antimicrobial activity and volatile constituents of the essential oil of Pulsatilla albana from Iran.
PubMed:Intraspecific variability of the essential oil of Ziziphora clinopodioides ssp. rigida from Iran.
PubMed:UV-B modulates the interplay between terpenoids and flavonoids in peppermint (Mentha x piperita L.).
PubMed:Phytochemistry and nematicidal activity of the essential oils from 8 Greek Lamiaceae aromatic plants and 13 terpene components.
PubMed:Synthesis and properties of chiral pyrazolidines derived from (+)-pulegone.
PubMed:Composition and chemical variability of Mentha suaveolens ssp. suaveolens and M. suaveolens ssp. insularis from Corsica.
PubMed:[Studies on characteristics of volatile oil and micro-identification between Herba Pogostemonis and Herba Agastachis rugosae].
PubMed:Mathematical modeling-guided evaluation of biochemical, developmental, environmental, and genotypic determinants of essential oil composition and yield in peppermint leaves.
PubMed:A VCD robust mode analysis of induced chirality: the case of pulegone in chloroform.
PubMed:Acaricidal properties of the essential oil from Hesperozygis ringens (Lamiaceae) on the cattle tick Riphicephalus (Boophilus) microplus.
PubMed:Evidence for dopamine involvement in ambulation promoted by pulegone in mice.
PubMed:Chemical composition and antimicrobial and antioxidant activities of Mentha (longifolia L. and viridis) essential oils.
PubMed:Enhanced biotransformation of TCE using plant terpenoids in contaminated groundwater.
PubMed:Insecticidal activity of essential oils from native medicinal plants of Central Argentina against the house fly, Musca domestica (L.).
PubMed:Quantitative determination of pulegone in pennyroyal oil by FT-IR spectroscopy.
PubMed:Determination of alkenylbenzenes and related flavour compounds in food samples by on-column preconcentration-capillary liquid chromatography.
PubMed:Chemical composition and in vitro antibacterial activity of the essential oil of Minthostachys mollis (Kunth) Griseb Vaught from the Venezuelan Andes.
PubMed:[Comparison on agronomy and quality characters of selective strain of Schizonepeta tenuifolia].
PubMed:A trapping method for semi-quantitative assessment of reactive metabolite formation using [35S]cysteine and [14C]cyanide.
PubMed:Influence of growth phase on the essential oil composition of Ziziphora clinopodioides Lam.
PubMed:Acetylcholinesterase inhibitory and antioxidant properties of Cyclotrichium niveum, Thymus praecox subsp. caucasicus var. caucasicus, Echinacea purpurea and E. pallida.
PubMed:Pediculus humanus capitis (head lice) and Pediculus humanus humanus (body lice): response to laboratory temperature and humidity and susceptibility to monoterpenoids.
PubMed:Structure and spasmolytic activity relationships of monoterpene analogues found in many aromatic plants.
PubMed:Calcium blocking activity as a mechanism of the spasmolytic effect of the essential oil of Calamintha glandulosa Silic on the isolated rat ileum.
PubMed:Larvicidal and oviposition-altering activity of monoterpenoids, trans-anithole and rosemary oil to the yellow fever mosquito Aedes aegypti (Diptera: Culicidae).
PubMed:Supercritical carbon dioxide extraction of Mentha pulegium L. essential oil.
PubMed:Defense on the rocks: low monoterpenoid levels in plants on pillars without mammalian herbivores.
PubMed:Antimicrobial activity and chemical composition of Mentha pulegium L. essential oil.
PubMed:Immunomodulatory effect of Schizonepeta tenuifolia water extract on mouse Th1/Th2 cytokine production in-vivo and in-vitro.
PubMed:Solvent effects on IR and VCD spectra of natural products: an experimental and theoretical VCD study of pulegone.
PubMed:Total synthesis and structural confirmation of ent-galbanic acid and marneral.
PubMed:Total synthesis of (+)-fawcettidine.
PubMed:Enantiospecific effect of pulegone and pulegone-derived lactones on Myzus persicae (Sulz.) settling and feeding.
PubMed:A systems biology approach identifies the biochemical mechanisms regulating monoterpenoid essential oil composition in peppermint.
PubMed:In silico toxicological screening of natural products.
PubMed:Insecticidal activity of menthol derivatives against mosquitoes.
PubMed:An enone reductase from Nicotiana tabacum: cDNA cloning, expression in Escherichia coli, and reduction of enones with the recombinant proteins.
PubMed:Convenient preparative method for lactones from 3-hydroxy propanoic acids using iodine under solvent-free conditions.
PubMed:Metabolic activation of herbal and dietary constituents and its clinical and toxicological implications: an update.
PubMed:14C-labeled pulegone and metabolites binding to alpha2u-globulin in kidneys of male F-344 rats.
PubMed:Composition and antifungal activity of the essential oil of Mentha cervina from Portugal.
PubMed:Antinociceptive activity of structural analogues of rotundifolone: structure-activity relationship.
PubMed:Volatile terpenoids of endophyte-free and infected peppermint (Mentha piperita L.): chemical partitioning of a symbiosis.
PubMed:Antibacterial activity and composition of the essential oil of Ziziphora clinopodioides subsp. bungeana (Juz.) Rech. f. from Iran.
PubMed:Fumigant activity of plant essential oils and components from Schizonepeta tenuifolia against Lycoriella ingenua (Diptera: Sciaridae).
PubMed:Quantification of flavor-related compounds in the unburned contents of bidi and clove cigarettes.
PubMed:Acaricidal effects of herb essential oils against Dermatophagoides farinae and D. pteronyssinus (Acari: Pyroglyphidae) and qualitative analysis of a herb Mentha pulegium(pennyroyal).
PubMed:[GC-MS analysis of volatile oil from the ear of Schizonepeta tenifolia Briq].
PubMed:Acaricidal activities of paeonol and benzoic acid from Paeonia suffruticosa root bark and monoterpenoids against Tyrophagus putrescentiae (Acari: Acaridae).
PubMed:The chemical composition of essential oil and in vitro antibacterial activities of essential oil and methanol extract of Ziziphora persica Bunge.
PubMed:[Comparison of supercritical fluid extraction and steam distillation methods for the extraction of essential oils from Schizonepeta tenuifolia Briq].
PubMed:Chemical composition of the essential oil of Salvia microstegia Boiss. et Balansa growing wild in Lebanon.
PubMed:On the mechanism of the Skraup-Doebner-Von Miller quinoline synthesis.
PubMed:Essential oil of the Persian sage, Salvia rhytidea Benth.
PubMed:Comparison of estimated daily intakes of flavouring substances with no-observed-effect levels.
PubMed:Essential oil composition, antibacterial and antioxidant activity of the oil and various extracts of Ziziphora clinopodioides subsp. rigida (BOISS.) RECH. f. from Iran.
PubMed:Vapor phase toxicity of marjoram oil compounds and their related monoterpenoids to Blattella germanica (Orthoptera: Blattellidae).
PubMed:Immunomodulating properties of Minthostachys verticillata on human lymphocytes and basophils.
PubMed:New monoterpenes from Mentha microphylla.
PubMed:Effects of mechanical wounding on essential oil composition and emission of volatiles from Minthostachys mollis.
PubMed:Quantitative variations in the essential oil of Minthostachys mollis (Kunth.) Griseb. in response to insects with different feeding habits.
PubMed:[Quantitative analysis of pulegone in Herba Schizonepetae].
PubMed:Analysis of pulegone and its enanthiomeric distribution in mint-flavoured food products.
PubMed:Analysis of volatile components from Ziziphora taurica subsp. taurica by steam distillation, superheated-water extraction, and direct thermal desorption with GCxGC-TOFMS.
PubMed:Dansyl glutathione as a trapping agent for the quantitative estimation and identification of reactive metabolites.
PubMed:Inhibitory effects of the essential oil of Mentha pulegium on the isolated rat myometrium.
PubMed:Toxic and repellent effects of Baccharis salicifolia essential oil on Tribolium castaneum.
PubMed:Photoelectron spectroscopy of natural products: terpenes.
PubMed:Organization of monoterpene biosynthesis in Mentha. Immunocytochemical localizations of geranyl diphosphate synthase, limonene-6-hydroxylase, isopiperitenol dehydrogenase, and pulegone reductase.
PubMed:PuPHOS: a synthetically useful chiral bidentate ligand for the intermolecular Pauson-Khand reaction.
PubMed:The constituents of essential oil and in vitro antimicrobial activity of Micromeria cilicica from Turkey.
PubMed:The effect of pretreatment with terpenes on transdermal iontophoretic delivery of arginine vasopressin.
PubMed:Acute liver failure associated with the use of herbal preparations containing black cohosh.
PubMed:Lactones. 21. Synthesis and odoriferous properties of lactones with the p-menthane system.
PubMed:Transdermal delivery of zidovudine: effect of terpenes and their mechanism of action.
PubMed:Tetrahydroacridin-9-ones, 9-chlorotetrahydroacridines, 9-amino-tetrahydroacridines and 9-(pyrazol-1-yl)-tetrahydroacridines derived from chiral cyclanones.
PubMed:Herbal bioactivation: the good, the bad and the ugly.
PubMed:Menthofuran regulates essential oil biosynthesis in peppermint by controlling a downstream monoterpene reductase.
PubMed:Synthesis of a highly hindered hydrindanone via alpha-carbonyl radical cyclization: enantiospecific formal syntheses of (-)-pinguisenol and (-)-alpha-pinguisene.
PubMed:In vivo studies on the metabolism of the monoterpene pulegone in humans using the metabolism of ingestion-correlated amounts (MICA) approach: explanation for the toxicity differences between (S)-(-)- and (R)-(+)-pulegone.
PubMed:Mitigation of pennyroyal oil hepatotoxicity in the mouse.
PubMed:Monoterpene double-bond reductases of the (-)-menthol biosynthetic pathway: isolation and characterization of cDNAs encoding (-)-isopiperitenone reductase and (+)-pulegone reductase of peppermint.
PubMed:Metabolism of (R)-(+)-menthofuran in Fischer-344 rats: identification of sulfonic acid metabolites.
PubMed:Chiral recognition ability of alpha-cyclodextrin with regard to some monoterpenoids under gas-liquid chromatographic conditions.
PubMed:New 1,3-oxathianes derived from myrtenal: synthesis and reactivity.
PubMed:Comparative disposition of (R)-(+)-pulegone in B6C3F1 mice and F344 rats.
PubMed:Composition of the essential oil of Mentha microphylla from the Gennargentu Mountains (Sardinia, Italy).
PubMed:Photoactive extracts from Thevetia peruviana with antifungal properties against Cladosporium cucumerinum.
PubMed:Transdermal iontophoresis of insulin. V. Effect of terpenes.
PubMed:Total synthesis of (+)-phomactin a using a B-alkyl Suzuki macrocyclization.
PubMed:Essential oil composition and antioxidant activity of endemic Ziziphora taurica subsp. cleonioides.
PubMed:Concentrations of nine alkenylbenzenes, coumarin, piperonal and pulegone in Indian bidi cigarette tobacco.
PubMed:An efficient procedure for the preparation of (E)-alpha-alkylidenecycloalkanones mediated by a CeCl(3) x 7H(2)O-NaI system. Novel methodology for the synthesis of (S)-(-)-pulegone.
PubMed:Antibacterial and antifungal activity of essential oils of Mentha suaveolens.
PubMed:The chemical constituents and biological activity of essential oil of Lavandula stoechas ssp. stoechas.
PubMed:Synthesis of termini-differentiated 6-carbon stereotetrads: an alkylative oxidation strategy for preparation of the c21-c26 segment of apoptolidin(1).
PubMed:Revision of the absolute configuration of the tricyclic sesquiterpene (+)-kelsoene by chemical correlation and enantiospecific total synthesis of its enantiomer.
PubMed:Stereoselective hydroxylation of 4-methyl-2-cyclohexenone in rats: its relevance to R-(+)-pulegone-mediated hepatotoxicity.
PubMed:Characterization of essential oils from lamiaceae species by fourier transform Raman spectroscopy.
PubMed:Phytochemical induction by herbivores could affect quality of essential oils from aromatic plants.
PubMed:Molecular cloning, functional expression and characterization of d-limonene synthase from Agastache rugosa.
PubMed:Menthone and isomenthone biosynthesis in Pelargonium tomentosum Jacq.
PubMed:Organogenesis and terpenoid synthesis in Mentha arvensis.
PubMed:Final report on the safety assessment of Mentha Piperita (Peppermint) Oil, Mentha Piperita (Peppermint) Leaf Extract, Mentha Piperita (Peppermint) Leaf, and Mentha Piperita (Peppermint) Leaf Water.
PubMed:Metabolism of (R)-(+)-pulegone in F344 rats.
PubMed:Effect of Mentha x piperita essential oil and monoterpenes on cucumber root membrane potential.
PubMed:The Principle of Maximum Chiral Discrimination: Chiral Recognition in Permethyl-beta-cyclodextrin.
PubMed:Synthesis of (+)-galiellalactone. Absolute configuration of galiellalactone.
PubMed:Ambulation-promoting effect of peppermint oil and identification of its active constituents.
PubMed:[Determination of the antibacterial and antiviral activity of the essential oil from Minthostachys verticillata (Griseb.) Epling].
PubMed:Chiral auxiliaries for asymmetric radical cyclization reactions: application to the enantioselective synthesis of (+)-triptocallol.
PubMed:First enantioselective syntheses of (+)- and (-)-wilforonide by using chiral auxiliaries derived from the same chiral source.
PubMed:Demonstration that menthofuran synthase of mint (Mentha) is a cytochrome P450 monooxygenase: cloning, functional expression, and characterization of the responsible gene.
PubMed:Hydroquinone derivatives and monoterpenoids from the Neotropical liverwort Plagiochila rutilans.
PubMed:Effect of ring size in R-(+)-pulegone-mediated hepatotoxicity: studies on the metabolism of R-(+)-4-methyl-2-(1-methylethylidene)-cyclopentanone and DL-camphorone in rats.
PubMed:Different stereoselectivity in the reduction of pulegone by Mentha species.
PubMed:Effect of (+)-pulegone and other oil components of Mentha x Piperita on cucumber respiration.
PubMed:Synthetic studies of the HIV-1 protease inhibitive didemnaketals: stereocontrolled synthetic approach to the key mother spiroketals.
PubMed:Biotransformation of constituents of essential oils by germinating wheat seed.
PubMed:Acaricidal activity of natural monoterpenes on Tyrophagus putrescentiae (Schrank), a mite of stored food.
PubMed:Suppression of the furylfuramide-induced SOS response by monoterpenoids with a p-menthane skeleton using the Salmonella typhimurium TA1535/pSK1002 Umu test.
PubMed:The use of linear expressions of solute boiling point versus retention to indicate special interactions with the molecular rings of modified cyclodextrin phases in gas chromatography
PubMed:Volatile constituents of Cunila polyantha (Lamiaceae) from Costa Rica. A rich source of menthone.
PubMed:Role of C-5 chiral center in R-(+)-pulegone-mediated hepatotoxicity: metabolic disposition and toxicity of 5, 5-dimethyl-2-(1-Methylethylidene)-cyclohexanone in rats.
PubMed:Biogenetic studies in Mentha x piperita. 2. Stereoselectivity in the bioconversion of pulegone into menthone and isomenthone.
PubMed:Biogenetic studies in Mentha x piperita. 1. deuterium-labeled monoterpene ketones: synthesis and stereoselective analysis.
PubMed:Transformation of a monoterpene ketone, (R)-(+)-pulegone, a potent hepatotoxin, in Mucor piriformis.
PubMed:Biosynthesis of menthofuran in Mentha x piperita: stereoselective and mechanistic studies.
PubMed:Solid phase microextraction of alkenylbenzenes and other flavor-related compounds from tobacco for analysis by selected ion monitoring gas chromatography-mass spectrometry.
PubMed:Glutathione S-transferase catalyzes the isomerization of (R)-2-hydroxymenthofuran to mintlactones.
PubMed:Plant-induced seizures: reappearance of an old problem.
PubMed:Transformation of the limonene synthase gene into peppermint (Mentha piperita L.) and preliminary studies on the essential oil profiles of single transgenic plants.
PubMed:Antimicrobial activity of the essential oil of Calamintha nepeta and its constituent pulegone against bacteria and fungi.
PubMed:Shade-avoidance responses in two common coastal redwood forest species, Sequoia sempervirens (Taxodiaceae) and Satureja douglasii (Lamiaceae), occurring in various light quality environments.
PubMed:Metabolism of (R)-(+)-pulegone and (R)-(+)-menthofuran by human liver cytochrome P-450s: evidence for formation of a furan epoxide.
PubMed:Metabolic disposition of a monoterpene ketone, piperitenone, in rats: evidence for the formation of a known toxin, p-cresol.
PubMed:Metabolic fate of S-(-)-pulegone in rat.
PubMed:Hepatoprotective effect of C-phycocyanin: protection for carbon tetrachloride and R-(+)-pulegone-mediated hepatotoxicty in rats.
PubMed:Lack of histological cerebellar changes in Wistar rats given pulegone for 28 days. Comparison of immersion and perfusion tissue fixation.
PubMed:Insecticidal activity of monoterpenoids to western corn rootworm (Coleoptera: Chrysomelidae), twospotted spider mite (Acari: Tetranychidae), and house fly (Diptera: Muscidae).
PubMed:Multiple organ failure after ingestion of pennyroyal oil from herbal tea in two infants.
PubMed:Chemical constituents of essential oils of muña, Bolivian plants traditionally used as pesticides, and their insecticidal properties against Chagas' disease vectors.
PubMed:Pine needle oil causes avoidance behaviors in pocket gopherGeomys bursarius.
PubMed:Pennyroyal toxicity: measurement of toxic metabolite levels in two cases and review of the literature.
PubMed:Mechanisms of the formation and disposition of reactive metabolites that can cause acute liver injury.
PubMed:Insecticidal properties of several monoterpenoids to the house fly (Diptera: Muscidae), red flour beetle (Coleoptera: Tenebrionidae), and southern corn rootworm (Coleoptera: Chrysomelidae).
PubMed:Synthesis, antiviral activity, and bioavailability studies of gamma-lactam derived HIV protease inhibitors.
PubMed:Antimicrobial activity of essential oil from Micromeria thymifolia (Scop.) Fritsch.
PubMed:Studies on the metabolism of a monoterpene ketone, R-(+)-pulegone--a hepatotoxin in rat: isolation and characterization of new metabolites.
PubMed:Inhibition of crystallins-induced inflammation in rabbit eyes with five phytogenic compounds.
PubMed:The volatiles of two bystropogon species from the canary islands (Spain).
PubMed:Investigations of mechanisms of reactive metabolite formation from (R)-(+)-pulegone.
PubMed:Reactive intermediates in the oxidation of menthofuran by cytochromes P-450.
PubMed:Partial characterization of biliary metabolites of pulegone by tandem mass spectrometry. Detection of glucuronide, glutathione, and glutathionyl glucuronide conjugates.
PubMed:Chemical, physiological, and toxicological aspects of the essential oil of some species of the genus Bystropogon.
PubMed:Evidence for the formation of a known toxin, p-cresol, from menthofuran.
PubMed:Biotransformations of R-(+)-pulegone and menthofuran in vitro: chemical basis for toxicity.
PubMed:Menthofuran-dependent and independent aspects of pulegone hepatotoxicity: roles of glutathione.
PubMed:The Essential Oil of Poliomintha incana.
PubMed:Antihistaminic activity of pulegone on the guinea-pig ileum.
PubMed:Metabolic activation of (R)-(+)-pulegone to a reactive enonal that covalently binds to mouse liver proteins.
PubMed:Hepatotoxicity of pulegone in rats: its effects on microsomal enzymes, in vivo.
PubMed:Sedating and antipyretic activity of the essential oil of Calamintha sylvatica subsp. ascendens.
PubMed:Metabolism of a monoterpene ketone, R-(+)-pulegone--a hepatotoxin in rat.
PubMed:Pulegone mediated hepatotoxicity: evidence for covalent binding of R(+)-[14C]pulegone to microsomal proteins in vitro.
PubMed:The Volatile Constituents of Ziziphora taurica subsp. cleonioides.
PubMed:Contribution of menthofuran to the hepatotoxicity of pulegone: assessment based on matched area under the curve and on matched time course.
PubMed:Effects of drug metabolism modifiers on pulegone-induced hepatotoxicity in mice.
PubMed:The metabolism of the abortifacient terpene, (R)-(+)-pulegone, to a proximate toxin, menthofuran.
PubMed:Synthesis of racemate and enantiomers of 15-methyltritriacontane, sex-stimulant pheromone of stable flyStomoxys calcitrans L.
PubMed:Metabolism of monoterpenes: demonstration that (+)-cis-isopulegone, not piperitenone, is the key intermediate in the conversion of (-)-isopiperitenone to (+)-pulegone in peppermint (Mentha piperita).
PubMed:[Determination of pulegone in the essential oil of Mentha pulegium L. from Chile].
PubMed:[Components of essential oils from different parts and the charcoal of Schizonepeta tenuifolia].
PubMed:In vivo and in vitro destruction of rat liver cytochrome P-450 by a monoterpene ketone, pulegone.
PubMed:Quantitative analysis of alpha, beta-thujone, pulegone, safrole, coumarin and beta-asarone in alcoholic beverages by selected-ion monitoring.
PubMed:Mutagenic investigation of peppermint oil in the Salmonella/mammalian-microsome test.
PubMed:Short term toxicity study in rats dosed with pulegone and menthol.
PubMed:Biotransformation by plant cells immobilized in cross-linked polyacrylamide-hydrazide.
PubMed:Biotransformation of monoterpenes by Mentha cell lines.
PubMed:Mammalian drug metabolism.
PubMed:Demonstration that limonene is the first cyclic intermediate in the biosynthesis of oxygenated p-menthane monoterpenes in Mentha piperita and other Mentha species.
PubMed:Biotransformation of monoterpenes by mentha cell lines: conversion of menthone to neomenthol.
PubMed:Biotransformation of monoterpenes by mentha cell lines: conversion of pulegone to isomenthone.
PubMed:Genetic basis for high limonene-cineole content of exceptional Mentha citrata hybrids.
PubMed:Effects of light and temperature on the monoterpenes of peppermint.
PubMed:[Colorimetric estimation of d-pulegone with 3, 5-dinitrobenzoic acid].
 
Notes:
component of peppermint oil.
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