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

diosphenol
(+/-)-2-hydroxypiperitone

Supplier Sponsors

Name:2-hydroxy-3-methyl-6-propan-2-ylcyclohex-2-en-1-one
CAS Number: 490-03-9Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:207-704-9
FDA UNII:4221SIG7EK
Nikkaji Web:J6.041K
XlogP3-AA:2.00 (est)
Molecular Weight:168.23592000
Formula:C10 H16 O2
NMR Predictor:Predict (works with chrome or firefox)
EFSA/JECFA Comments:
Racemate (EFFA, 2010a).
Category:flavor and 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
JECFA Food Flavoring:2038 (+/-)-2-hydroxypiperitone
FLAVIS Number:07.168 (Old)
DG SANTE Food Flavourings:07.168 2-hydroxypiperitone
FEMA Number:4143 (+/-)-2-hydroxypiperitone
FDA:No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm (SATF):490-03-9 ; (+/-)-2-HYDROXYPIPERITONE
 
Physical Properties:
Appearance:colorless to pale yellow crystals (est)
Assay: 98.00 to 100.00
Food Chemicals Codex Listed: No
Specific Gravity:0.95240 @ 25.00 °C.
Refractive Index:1.46079 @ 20.00 °C.
Melting Point: 82.00 °C. @ 760.00 mm Hg
Boiling Point: 233.00 °C. @ 760.00 mm Hg
Vapor Pressure:0.000310 mmHg @ 25.00 °C. (est)
Flash Point:> 200.00 °F. TCC ( > 93.33 °C. )
logP (o/w): 1.072 (est)
Soluble in:
 alcohol
 water, 139.7 mg/L @ 25 °C (est)
Insoluble in:
 water
 
Organoleptic Properties:
Odor Type: minty
Odor Strength:high ,
recommend smelling in a 0.10 % solution or less
minty buchu leafy currant bud black currant bud
Odor Description:at 0.10 % in dipropylene glycol. minty buchu leaves black currant
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
Berjé
Diosphenol Natural
Happening at Berje
Hermitage Oils
Diosphenol Natural Isolate
Odor: characteristic
Use: Obtained by rectification of Buchu betulina essential oil, light yellow in colour and of a waxy consistency in cold temperatures (with gentle warmth it quickly becomes pourable). Used in fragrance and cosmetic applications, imparting unique freshness, diffusive power and strength.
The Vault
Payand Betrand
Diosphenol South Africa, Natural Isolated Constituent
Penta International
2-HYDROXYPIPERITONE
Reincke & Fichtner
Diosphenole natural
 
Safety Information:
 
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:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category: flavor and fragrance agents
Recommendation for diosphenol usage levels up to:
  0.3000 % in the fragrance concentrate.
 
Maximised Survey-derived Daily Intakes (MSDI-EU): 0.0012 (μg/capita/day)
Modified Theoretical Added Maximum Daily Intake (mTAMDI): 1600 (μg/person/day)
Threshold of Concern:90 (μg/person/day)
Structure Class: III
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: 22
 average usual ppmaverage maximum ppm
baked goods: 5.0000025.00000
beverages(nonalcoholic): --
beverages(alcoholic): --
breakfast cereal: 2.0000010.00000
cheese: 3.0000015.00000
chewing gum: --
condiments / relishes: 2.0000010.00000
confectionery froastings: 4.0000020.00000
egg products: --
fats / oils: 2.0000010.00000
fish products: 1.000005.00000
frozen dairy: 3.0000015.00000
fruit ices: 3.0000015.00000
gelatins / puddings: --
granulated sugar: --
gravies: --
hard candy: --
imitation dairy: 3.0000015.00000
instant coffee / tea: --
jams / jellies: --
meat products: 1.000005.00000
milk products: 3.0000015.00000
nut products: --
other grains: --
poultry: --
processed fruits: 2.0000010.00000
processed vegetables: --
reconstituted vegetables: --
seasonings / flavors: 2.0000010.00000
snack foods: 5.0000025.00000
soft candy: --
soups: 2.0000010.00000
sugar substitutes: --
sweet sauces: 2.0000010.00000
 
Food categories according to Commission Regulation EC No. 1565/2000 (EC, 2000) in FGE.06 (EFSA, 2002a). According to the Industry the "normal" use is defined as the average of reported usages and "maximum use" is defined as the 95th percentile of reported usages (EFSA, 2002i).
Note: mg/kg = 0.001/1000 = 0.000001 = 1/1000000 = ppm.
 average usage mg/kgmaximum usage mg/kg
Dairy products, excluding products of category 02.0 (01.0): 3.0000015.00000
Fats and oils, and fat emulsions (type water-in-oil) (02.0): 2.0000010.00000
Edible ices, including sherbet and sorbet (03.0): 3.0000015.00000
Processed fruit (04.1): 2.0000010.00000
Processed vegetables (incl. mushrooms & fungi, roots & tubers, pulses and legumes), and nuts & seeds (04.2): --
Confectionery (05.0): 4.0000020.00000
Cereals and cereal products, incl. flours & starches from roots & tubers, pulses & legumes, excluding bakery (06.0): 2.0000010.00000
Bakery wares (07.0): 5.0000025.00000
Meat and meat products, including poultry and game (08.0): 1.000005.00000
Fish and fish products, including molluscs, crustaceans and echinoderms (MCE) (09.0): 1.000005.00000
Eggs and egg products (10.0): --
Sweeteners, including honey (11.0): --
Salts, spices, soups, sauces, salads, protein products, etc. (12.0): 2.0000010.00000
Foodstuffs intended for particular nutritional uses (13.0): 3.0000015.00000
Non-alcoholic ("soft") beverages, excl. dairy products (14.1): 2.0000010.00000
Alcoholic beverages, incl. alcohol-free and low-alcoholic counterparts (14.2): 4.0000020.00000
Ready-to-eat savouries (15.0): 5.0000025.00000
Composite foods (e.g. casseroles, meat pies, mincemeat) - foods that could not be placed in categories 01.0 - 15.0 (16.0): 2.0000010.00000
 
Safety References:
European Food Safety Athority(efsa):Flavor usage levels; Subacute, Subchronic, Chronic and Carcinogenicity Studies; Developmental / Reproductive Toxicity Studies; Genotoxicity Studies...

European Food Safety Authority (EFSA) reference(s):

Flavouring Group Evaluation 213: alpha,beta-Unsaturated alicyclic ketones and precursors from chemical subgroup 2.7 of FGE.19
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 11, Revision 2 (FGE.11Rev2): Aliphatic dialcohols, diketones, and hydroxyketones from chemical groups 8 and 10
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 11, Revision 3 (FGE.11Rev3): Aliphatic dialcohols, diketones, and hydroxyketones from chemical groups 8 and 10
View page or View pdf

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

EPI System: View
EPA Substance Registry Services (TSCA):490-03-9
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :79023
National Institute of Allergy and Infectious Diseases:Data
2-hydroxy-3-methyl-6-propan-2-ylcyclohex-2-en-1-one
Chemidplus:0000490039
 
References:
Leffingwell:Chirality or Article
 2-hydroxy-3-methyl-6-propan-2-ylcyclohex-2-en-1-one
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:490-03-9
Pubchem (cid):79023
Pubchem (sid):135036087
Pherobase:View
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2009
(IUPAC):Atomic Weights of the Elements 2009 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
FDA Substances Added to Food (formerly EAFUS):View
CHEBI:View
KEGG (GenomeNet):C09854
HMDB (The Human Metabolome Database):HMDB37014
FooDB:FDB009611
Typical G.C.
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
RSC Learn Chemistry:View
FAO:(+/-)-2-Hydroxypiperitone
 
Potential Blenders and core components note
For Odor
citrus
bergamot acetoacetate
FR
floral
cassis buteneone
FR
cassis cyclohexene
FR
cassis oxime 10%
FR
delta-
damascone
FL/FR
fruity
(Z)-beta-
damascone
FL/FR
dimethyl benzyl carbinyl isobutyrate
FR
herbal
barosma betulina leaf oil
FL/FR
buchu leaf absolute
FL/FR
(2S,5R)-
buchu mercaptan
FL/FR
buchu mercaptan acetate
FL/FR
buchu oxime
FR
methyl ortho-anisate
FL/FR
mentholic
(±)-iso
menthone
FL/FR
laevo-
menthyl acetate
FL/FR
minty
agathosma crenulata leaf oil
FL/FR
(-)-
menthone
FL/FR
(±)-
menthone
FL/FR
(R)-(+)-
pulegone
FR
sulfurous
buchu mercaptan
FL/FR
mango thiol
FL/FR
4-
methoxy-2-methyl butane thiol
FL/FR
4-
methyl 4-mercaptopentan-2-one 1% solution
FL/FR
passiflora acetate
FL/FR
For Flavor
No flavor group found for these
4-
methyl 4-mercaptopentan-2-one 1% solution
FL/FR
methyl ortho-anisate
FL/FR
fruity
fruity
buchu mercaptan acetate
FL/FR
(Z)-beta-
damascone
FL/FR
herbal
barosma betulina leaf oil
FL/FR
buchu leaf absolute
FL/FR
(2S,5R)-
buchu mercaptan
FL/FR
buchu oil fractions
FL
minty
agathosma crenulata leaf oil
FL/FR
(±)-iso
menthone
FL/FR
(±)-
menthone
FL/FR
(-)-
menthone
FL/FR
laevo-
menthyl acetate
FL/FR
sulfurous
buchu leaf distillates
FL
buchu mercaptan
FL/FR
mango thiol
FL/FR
4-
methoxy-2-methyl butane thiol
FL/FR
tropical
passiflora acetate
FL/FR
vegetable
potato butyraldehyde
FL
woody
delta-
damascone
FL/FR
 
Potential Uses:
FLbuchu leaf
FRcurrant black currant
FRfloral
 
Occurrence (nature, food, other):note
 buchu leaf
Search Trop Picture
 buchu leaf oil @ 22.30%
Data GC Search Trop Picture
 currant black currant buds - 36 mg/kg
Search Trop Picture
 horsemint shoot
Search Trop Picture
 peppermint leaf
Search Trop Picture
 
Synonyms:
 barosma camphor
 buccocamphor
 buchu camphor
2-cyclohexen-1-one, 2-hydroxy-3-methyl-6-(1-methylethyl)-
 diosphenol natural
 diosphenol south africa, natural isolated constituent
2-hydroxy-3-methyl-6-(1-methyl ethyl)-2-cyclohexen-1-one
2-hydroxy-3-methyl-6-(1-methylethyl)-2-cyclohexen-1-one
2-hydroxy-3-methyl-6-(propan-2-yl)cyclohex-2-en-1-one
2-hydroxy-3-methyl-6-propan-2-ylcyclohex-2-en-1-one
2-hydroxy-6-(isopropyl)-3-methyl cyclohex-2-en-1-one
2-hydroxy-6-(isopropyl)-3-methylcyclohex-2-en-1-one
2-hydroxy-6-isopropyl-3-methyl-2-cyclohexen-1-one
2-hydroxy-6-isopropyl-3-methylcyclohex-2-en-1-one
(+/-)-2-hydroxypiperitone
(±)-2-hydroxypiperitone
2-hydroxypiperitone
1-p-menthen-2-ol-3-one
1-methyl-4-isopropyl-1-cyclohexen-2-ol-3-one
 

Articles:

PubMed:In silico exploration of novel phytoligands against probable drug target of Clostridium tetani.
PubMed:In vitro antitrypanosomal activities of quassinoid compounds from the fruits of a medicinal plant, Brucea javanica.
PubMed:Antibacterial activities and cytotoxicity of terpenoids isolated from Spirostachys africana.
PubMed:A diosphenol-based strategy for the total synthesis of (-)-terpestacin.
PubMed:ent-Beyerane diterpenoids from the heartwood of Excoecaria parvifolia.
PubMed:Diosphenol-based approach to the a-ring functionalization of advanced Taxol precursors.
PubMed:Conversion of quassinoids for enhancement of inhibitory effect against Epstein-Barr virus early antigen activation. Introduction of lipophilic side chain and esterification of diosphenol.
PubMed:Studies directed toward synthesis of quassinoids VII. Conversion of chenodeoxycholic acid to a delta-lactone quassinoid analog and generation of A-ring diosphenol acetate derivatives of deoxycholic acid.
PubMed:The effect of steroidal diosphenol agents on advanced breast cancer.
 
Notes:
None found
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