apiole (parsley)
1,3-benzodioxole, 4,7-dimethoxy-5-(2-propenyl)-
 
Notes:
crystalline essential oil isolated directly from commercial oil of parsley. Occurs in Sassafras albidum (sassafras) and Anethum graveolens (dill) Apiol is an organic chemical compound, also known as parsley apiol, apiole or parsley camphor. It is found in celery, parsley seeds, and the essential oil of parsley. Heinrich Christoph Link, an apothecary in Leipzig, discovered the substance in 1715 as greenish crystals reduced by steam from oil of parsley. In 1855 Joret and Homolle discovered that apiol was an effective treatment of amenorrea or lack of menstruation.; In medicine it has been used, as essential oil or in purified form, for the treatment of menstrual disorders. It is an irritant and in high doses it is toxic and can cause liver and kidney damage.
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4,7-dimethoxy-5-prop-2-enyl-1,3-benzodioxole (Click)
CAS Number: 523-80-8Picture of molecule
ECHA EINECS - REACH Pre-Reg: 208-349-2
FDA UNII: QQ67504PXO
Nikkaji Web: J6.635D
Beilstein Number: 0195747
XlogP3-AA: 2.70 (est)
Molecular Weight: 222.24038000
Formula: C12 H14 O4
BioActivity Summary: listing
NMR Predictor: Predict (works with chrome or firefox)
Category: natural substances and extractives
 
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JECFA Food Flavoring: 1787  apiole
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Physical Properties:
Appearance: colorless to yellow green clear liquid (est)
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Specific Gravity: 1.12400 to 1.43500 @  25.00 °C.
Pounds per Gallon - (est).: 9.353 to 11.941
Refractive Index: 1.53600 to 1.53800 @  20.00 °C.
Melting Point: 29.00 to  30.00 °C. @ 760.00 mm Hg
Boiling Point: 294.00 to  295.00 °C. @ 760.00 mm Hg
Boiling Point: 159.00 to  160.00 °C. @ 10.00 mm Hg
Vapor Pressure: 0.003000 mm/Hg @ 25.00 °C. (est)
Flash Point: 243.00 °F. TCC ( 117.20 °C. ) (est)
logP (o/w): 3.481 (est)
Soluble in:
 alcohol
 acetone
 ether
 acetic acid
 water, 27.68 mg/L @ 25 °C (est)
Insoluble in:
 water
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Organoleptic Properties:
Odor Type: herbal
Odor Strength: low
 parsley  herbal  
Odor Description:
at 100.00 %. 
parsley faint
  
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Cosmetic Information:
None found
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Suppliers:
ExtraSynthese
For experimental / research use only.
Apiole (GC) ≥99%
Santa Cruz Biotechnology
For experimental / research use only.
Apioline
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Safety Information:
Preferred SDS: View
 
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:
subcutaneous-frog LDLo 1515 mg/kg
PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)
Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 35, Pg. 342, 1895.

subcutaneous-mouse LDLo 1000 mg/kg
Bolletino della Societe Italiana di Biologia Sperimentale. Vol. 14, Pg. 291, 1939.

Inhalation Toxicity:
Not determined
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Safety in Use Information:
Category: natural substances and extractives
Recommendation for apiole (parsley) usage levels up to:
 not for fragrance use.
 
Recommendation for apiole (parsley) flavor usage levels up to:
 not for flavor use.
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Safety References:
EPI System: View
Cancer Citations: Search
Toxicology Citations: Search
Env. Mutagen Info. Center: Search
NLM Developmental and Reproductive Toxicity: Search
EPA Substance Registry Services (TSCA): 523-80-8
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 10659
National Institute of Allergy and Infectious Diseases: Data
 4,7-dimethoxy-5-prop-2-enyl-1,3-benzodioxole
Chemidplus: 0000523808
RTECS: CY2500000 for cas# 523-80-8
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References:
 4,7-dimethoxy-5-prop-2-enyl-1,3-benzodioxole
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 10659
Pubchem (sid): 134977796
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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
CHEBI: View
CHEMBL: View
KEGG (GenomeNet): C10429
HMDB (The Human Metabolome Database): HMDB33776
FooDB: FDB011929
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
Wikipedia: View
RSC Learn Chemistry: View
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Potential Blenders and core components note
 
For Odor
amber
amber
 angelica root oilFL/FR
animal
isobutyl quinolineFR
anisic
 estragoleFL/FR
balsamic
 cinnamyl formateFL/FR
camphoreous
 verbenoneFL/FR
caramellic
 fenugreek absoluteFL/FR
ethereal
 ethyl 4-pentenoateFL/FR
fatty
(E)-2-octenalFL/FR
floral
 dihydrorose oxideFR
 dimethyl benzyl carbinyl butyrateFL/FR
2,4-dimethyl-3-cyclohexene-1-methanolFR
 geranium oil africaFL/FR
 geranium oil egyptFL/FR
 hexahydrofarnesyl acetoneFL/FR
 jasmin pyranolFR
isojasmoneFL/FR
(Z)-jasmoneFL/FR
 neryl formateFL/FR
2-pentadecanoneFL/FR
2-pentyl cyclopentanoneFR
isophytolFL/FR
 rose pyranFR
fruity
 tropical indeneFR
green
isobutyl benzyl carbinolFL/FR
isobutyl heptanoateFL/FR
isobutyl methyl ketoneFL/FR
2-sec-butyl thiazoleFL/FR
 heptanal (aldehyde C-7)FL/FR
1-heptanolFL/FR
(Z)-4-hexen-1-olFL/FR
(E)-4-hexen-1-ol 
3-hexenyl 2-methyl butyrateFL/FR
 hexyl hexanoateFL/FR
english ivy leaf absoluteFR
 seaweed absolute (fucus vesiculosus et serratus)FL/FR
herbal
6-acetoxydihydrotheaspiraneFL/FR
alpha-amyl cinnamyl formateFL/FR
 anethum graveolens herb oilFL/FR
 anthemis nobilis flower oil romanFL/FR
 apium graveolens seed oil indiaFL/FR
sweet basil absoluteFL/FR
3-butyl phthalideFL/FR
3-butylidene phthalideFL/FR
(+)-alpha-campholenic aldehydeFL/FR
 celery ketoneFL/FR
 celery leaf oilFL/FR
 celery seed oil CO2 extractFL/FR
 celery undeceneFR
 dill weed oil cubaFL/FR
 dill weed oil reunionFL/FR
 dimethyl benzyl carbinyl formateFL/FR
cis-herbal cyclohexaneFR
 herbal dioxaneFR
 herbal heptaneFR
 hop absoluteFL/FR
 hop oilFL/FR
 levisticum officinale herb oilFL/FR
 levisticum officinale root absoluteFL/FR
 linalyl formateFL/FR
 linalyl octanoateFL/FR
 marigold oil mexicoFL/FR
 melaleuca leucadendron var. cajuputi leaf oilFL/FR
(E)-6-methyl-3-hepten-2-oneFL/FR
 mistletoe absolute 
 nonisyl formateFR
1-octen-3-yl acetateFL/FR
 origanum oilFL/FR
 origanum oil greeceFL/FR
 perillaldehydeFL/FR
3-propylidene phthalideFL/FR
 reseda absoluteFR
 tagete oil CO2 extractFL/FR
 tagete oil rwandaFL/FR
 tagete oil south africaFL/FR
 theaspiraneFL/FR
 tricyclodecyl acetateFR
 viridiflorolFL/FR
 wormwood oil americaFL/FR
minty
(-)-isopulegolFL/FR
mossy
 treemoss absoluteFR
pine
 dipentene terpene hydrocarbon byproductsFR
spicy
isobutyl angelateFL/FR
(-)-cubenolFL/FR
 cuminaldehydeFL/FR
isocyclogeraniol (IFF)FR
 levisticum officinale root oilFL/FR
tonka
 whiskey lactoneFL/FR
woody
 amber dodecaneFR
alpha-thujene 
 verdoxanFR
 
For Flavor
 
No flavor group found for these
6-acetoxydihydrotheaspiraneFL/FR
alpha-amyl cinnamyl formateFL/FR
isobutyl heptanoateFL/FR
3-butyl phthalideFL/FR
4-butyl thiazoleFL
2-sec-butyl thiazoleFL/FR
3-butylidene phthalideFL/FR
(+)-alpha-campholenic aldehydeFL/FR
 celery ketoneFL/FR
 cinnamyl formateFL/FR
 dimethyl benzyl carbinyl formateFL/FR
 ethyl 4-pentenoateFL/FR
 fig leaf absoluteFL
 heptanal (aldehyde C-7)FL/FR
(E,E)-2,4-hexadien-1-olFL
 hexahydrofarnesyl acetoneFL/FR
 linalyl formateFL/FR
 melaleuca leucadendron var. cajuputi leaf oilFL/FR
(E)-6-methyl-3-hepten-2-oneFL/FR
 mistletoe absolute 
2-propyl thiazoleFL
(-)-isopulegolFL/FR
 seaweed absolute (fucus vesiculosus et serratus)FL/FR
alpha-thujene 
 verbenoneFL/FR
 viridiflorolFL/FR
alliaceous
 cyclopentyl mercaptanFL
balsamic
isobutyl benzyl carbinolFL/FR
caramellic
 fenugreek absoluteFL/FR
cooling
 theaspiraneFL/FR
fatty
(E)-2-octenalFL/FR
2-pentadecanoneFL/FR
floral
 dimethyl benzyl carbinyl butyrateFL/FR
 geranium oil africaFL/FR
 geranium oil egyptFL/FR
fruity
 hexyl hexanoateFL/FR
 neryl formateFL/FR
 tagete oil CO2 extractFL/FR
 tagete oil rwandaFL/FR
 tagete oil south africaFL/FR
green
 angelica root oilFL/FR
isobutyl angelateFL/FR
isobutyl methyl ketoneFL/FR
(E)-4-hexen-1-ol 
(Z)-4-hexen-1-olFL/FR
3-hexenyl 2-methyl butyrateFL/FR
isojasmoneFL/FR
1-octen-3-yl acetateFL/FR
3-propylidene phthalideFL/FR
 sorbyl acetateFL
herbal
 anethum graveolens herb oilFL/FR
 anthemis nobilis flower oil romanFL/FR
 apium graveolens seed oil indiaFL/FR
sweet basil absoluteFL/FR
 celery leaf oilFL/FR
 celery seed oil CO2 extractFL/FR
 celery seed oleoresinFL
 dill weed oil cubaFL/FR
 dill weed oil reunionFL/FR
 hop absoluteFL/FR
 hop oilFL/FR
 linalyl octanoateFL/FR
 marigold oil mexicoFL/FR
 origanum oilFL/FR
 origanum oil greeceFL/FR
curled parsley seed oleoresinFL
 wormwood oil americaFL/FR
licorice
 estragoleFL/FR
oily
isophytolFL/FR
solvent
1-heptanolFL/FR
spicy
(-)-cubenolFL/FR
 cuminaldehydeFL/FR
 levisticum officinale herb oilFL/FR
 levisticum officinale oleoresinFL
 levisticum officinale root absoluteFL/FR
 levisticum officinale root oilFL/FR
 perillaldehydeFL/FR
woody
(Z)-jasmoneFL/FR
 whiskey lactoneFL/FR
 
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Potential Uses:
None Found
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Occurrence (nature, food, other): note
 celery seed
Search Trop  Picture
 dill oil
Search Trop  Picture
 dill root
Search Trop  Picture
 dill root oil
Search Trop  Picture
 dill seed
Search Trop  Picture
 dill shoot
Search Trop  Picture
 fennel seed
Search Trop  Picture
 lovage seed
Search Trop  Picture
 parsley
Search Trop  Picture
 parsley fruit
Search Trop  Picture
 parsley fruit oil
Search Trop  Picture
 parsley leaf
Search Trop  Picture
 parsley leaf oil
Search Trop  Picture
 parsley oil
Search Trop  Picture
 parsley rhizome
Search Trop  Picture
 parsley root
Search Trop  Picture
 parsley root oil
Search Trop  Picture
 parsley seed
Search Trop  Picture
 parsley seed oil
Search Trop  Picture
 parsley shoot
Search Trop  Picture
 sassafras
Search Trop  Picture
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Synonyms:
 allyl dimethoxymethylene dioxybenzene
1-allyl-2,5-dimethoxy-3,4-methylene dioxybenzene
1-allyl-2,5-dimethoxy-3,4-methylenedioxybenzene
5-allyl-4,7-dimethoxy-1,3-benzodioxol
 apiol (parsley)
 apioline (parsley)
1,3-benzodioxole, 4,7-dimethoxy-5-(2-propen-1-yl)-
1,3-benzodioxole, 4,7-dimethoxy-5-(2-propenyl)-
4,7-dimethoxy-5-(2-propenyl)-1,3-benzodioxole
4,7-dimethoxy-5-(prop-2-en-1-yl)-1,3-benzodioxole
4,7-dimethoxy-5-prop-2-enyl-1,3-benzodioxole
4,7-dimethoxy-5-prop-2-enyl-2H-benzo[d]1,3-dioxolene
1,2-methylene dioxy-3,6-dimethoxy-4-allyl benzene
 parsley apiol
 parsley apiole
 parsley camphor
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Articles:
PubMed: The in vivo antitumor effects on human COLO 205 cancer cells of the 4,7-dimethoxy-5-(2-propen-1-yl)-1,3-benzodioxole (apiole) derivative of 5-substituted 4,7-dimethoxy-5-methyl-l,3-benzodioxole (SY-1) isolated from the fruiting body of Antrodia camphorate.
PubMed: Age-dependent changes from allylphenol to prenylated benzoic acid production in Piper gaudichaudianum Kunth.
PubMed: Chemical composition, antimicrobial and antioxidant activities of the essential oil of Psammogeton canescens.
PubMed: [Poisoning by apiole. 3. Toxicological studies: Labat reaction and determination with chromotropic acid].
PubMed: [Poisoning by apiole. II. Histopathological aspects and pathogenetic discussion].
PubMed: [Quantitative determination of apiole].
PubMed: Psychotrophic phenylisopropylamines derived from apiole and dillapiole.
PubMed: Study of the Anti-Proliferative Activity of 5-Substituted 4,7-Dimethoxy-1,3-Benzodioxole Derivatives of SY-1 from Antrodia camphorata on Human COLO 205 Colon Cancer Cells.
PubMed: Medicinal plants from the genus Acalypha (Euphorbiaceae)--a review of their ethnopharmacology and phytochemistry.
PubMed: Endemic Balkan parsnip Pastinaca hirsuta: the chemical profile of essential oils, headspace volatiles and extracts.
PubMed: Critique of medicinal conspicuousness of Parsley(Petroselinum crispum): a culinary herb of Mediterranean region.
PubMed: Chemical composition of the essential oil of Pituranthos scoparius.
PubMed: Chemical and biological evaluation of essential oils from two species of Myrtaceae - Eugenia uniflora L. and Plinia trunciflora (O. Berg) Kausel.
PubMed: Antioxidant capacity and larvicidal and antifungal activities of essential oils and extracts from Piper krukoffii.
PubMed: Acaricidal activities of apiol and its derivatives from Petroselinum sativum seeds against Dermatophagoides pteronyssinus, Dermatophagoides farinae, and Tyrophagus putrescentiae.
PubMed: Chemical composition and antioxidant activities of the essential oil and methanol extracts of Psammogeton canescens.
PubMed: Antimicrobial activities of essential oil and hexane extract of Florence fennel [Foeniculum vulgare var. azoricum (Mill.) Thell.] against foodborne microorganisms.
PubMed: Comparative essential oil composition of flowers, leavesand stems of basil (Ocimum basilicum L.) used as herb.
PubMed: Biotransformation of menthol and geraniol by hairy root cultures of Anethum graveolens: effect on growth and volatile components.
PubMed: Essential oil composition of three Peperomia species from the Amazon, Brazil.
PubMed: Chemical composition and antimicrobial activities of the essential oil from the seeds of Enterolobium contortisiliquum (leguminosae).
PubMed: Chemical composition and antimicrobial activity of Momordica charantia seed essential oil.
PubMed: Comparative analysis of the oil and supercritical CO2 extract of Ridolfia segetum (L.) Moris.
PubMed: Inhibition of oxidation of human low-density lipoproteins by phenolic substances in different essential oils varieties.
PubMed: Compartive study of volatile components and fatty acids of plants and in vitro cultures of parsley (Petroselinum crispum (Mill) nym ex hill).
PubMed: Volatile chemical constituents of Piper aduncum L and Piper gibbilimbum C. DC (Piperaceae) from Papua New Guinea.
PubMed: Dillapiol and Apiol as specific inhibitors of the biosynthesis of aflatoxin G1 in Aspergillus parasiticus.
PubMed: Plant-derived natural products exhibiting activity against formosan subterranean termites (Coptotermes formosanus).
PubMed: Enzyme activity in the flesh fly Parasarcophaga dux Thomson influenced by dill compounds, myristicin and apiol.
PubMed: Toxicological efficacy of some indigenous dill compounds against the flesh fly, Parasarcophaga dux Thomson.
PubMed: Anaerobic utilization of essential oils by denitrifying bacteria.
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