apiole (parsley)

General Material Information

Preferred name	apiole (parsley)
Trivial Name	Apiole
Short Description	1,3-benzodioxole, 4,7-dimethoxy-5-(2-propenyl)-
Formula	C12 H14 O4
CAS Number	523-80-8
ECHA Number	208-349-2
FDA UNII	QQ67504PXO
Nikkaji Number	J6.635D
Beilstein Number	0195747
xLogP3-AA	2.70 (est)
Bio Activity Summary	External link
NMR Predictor	External link
JECFA Food Flavoring	1787 apiole
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 4,7-dimethoxy-5-prop-2-enyl-1,3-benzodioxole 1,3-Benzodioxole, 4,7-dimethoxy-5-(2-propen-1-yl)- Apiole Benzene, 1-allyl-2,5-dimethoxy-3,4-(methylenedioxy)- 1,3-Benzodioxole, 4,7-dimethoxy-5-(2-propenyl)- 4,7-Dimethoxy-5-(2-propen-1-yl)-1,3-benzodioxole 1-Allyl-2,5-dimethoxy-3,4-methylenedioxybenzene Apiol 1,2-Methylenedioxy-3,6-dimethoxy-4-allylbenzene Apioline 5-Allyl-4,7-dimethoxy-1,3-benzodioxole Petersilienapiol NSC 9070 4,7-Dimethoxy-5-(2-propenyl)-1,3-benzodioxole

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Literature & References

	4,7-dimethoxy-5-prop-2-enyl-1,3-benzodioxole
NIST Chemistry WebBook:	Search Inchi
Pubchem (cid):	10659
Pubchem (sid):	134977796

Publications by 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.
Age-dependent changes from allylphenol to prenylated benzoic acid production in Piper gaudichaudianum Kunth.
Chemical composition, antimicrobial and antioxidant activities of the essential oil of Psammogeton canescens.
[Poisoning by apiole. 3. Toxicological studies: Labat reaction and determination with chromotropic acid].
[Poisoning by apiole. II. Histopathological aspects and pathogenetic discussion].
[Quantitative determination of apiole].
Psychotrophic phenylisopropylamines derived from apiole and dillapiole.
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.
Medicinal plants from the genus Acalypha (Euphorbiaceae)--a review of their ethnopharmacology and phytochemistry.
Endemic Balkan parsnip Pastinaca hirsuta: the chemical profile of essential oils, headspace volatiles and extracts.
Critique of medicinal conspicuousness of Parsley(Petroselinum crispum): a culinary herb of Mediterranean region.
Chemical composition of the essential oil of Pituranthos scoparius.
Chemical and biological evaluation of essential oils from two species of Myrtaceae - Eugenia uniflora L. and Plinia trunciflora (O. Berg) Kausel.
Antioxidant capacity and larvicidal and antifungal activities of essential oils and extracts from Piper krukoffii.
Acaricidal activities of apiol and its derivatives from Petroselinum sativum seeds against Dermatophagoides pteronyssinus, Dermatophagoides farinae, and Tyrophagus putrescentiae.
Chemical composition and antioxidant activities of the essential oil and methanol extracts of Psammogeton canescens.
Antimicrobial activities of essential oil and hexane extract of Florence fennel [Foeniculum vulgare var. azoricum (Mill.) Thell.] against foodborne microorganisms.
Comparative essential oil composition of flowers, leavesand stems of basil (Ocimum basilicum L.) used as herb.
Biotransformation of menthol and geraniol by hairy root cultures of Anethum graveolens: effect on growth and volatile components.
Essential oil composition of three Peperomia species from the Amazon, Brazil.
Chemical composition and antimicrobial activities of the essential oil from the seeds of Enterolobium contortisiliquum (leguminosae).
Chemical composition and antimicrobial activity of Momordica charantia seed essential oil.
Comparative analysis of the oil and supercritical CO2 extract of Ridolfia segetum (L.) Moris.
Inhibition of oxidation of human low-density lipoproteins by phenolic substances in different essential oils varieties.
Compartive study of volatile components and fatty acids of plants and in vitro cultures of parsley (Petroselinum crispum (Mill) nym ex hill).
Volatile chemical constituents of Piper aduncum L and Piper gibbilimbum C. DC (Piperaceae) from Papua New Guinea.
Dillapiol and Apiol as specific inhibitors of the biosynthesis of aflatoxin G1 in Aspergillus parasiticus.
Plant-derived natural products exhibiting activity against formosan subterranean termites (Coptotermes formosanus).
Enzyme activity in the flesh fly Parasarcophaga dux Thomson influenced by dill compounds, myristicin and apiol.
Toxicological efficacy of some indigenous dill compounds against the flesh fly, Parasarcophaga dux Thomson.
Anaerobic utilization of essential oils by denitrifying bacteria.

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
KEGG (GenomeNet):	C10429
HMDB (The Human Metabolome Database):	HMDB33776
FooDB:	FDB011929
VCF-Online:	VCF Volatile Compounds in Food
ChemSpider:	View
Wikipedia:	View

Suppliers

BOC Sciences	ExtraSynthese
Santa Cruz Biotechnology

PhysChem Properties

Material listed in food chemical codex	No
Molecular weight	222.24038696289
Specific gravity	@ 25 °C
Pounds per Gallon	9.353 to 11.941
Refractive Index	1.536 to 1.538 @ 20 °C
Melting Point	29 to 30°C @ 760 mm Hg
Boiling Point	294 to 295°C @ 760 mm Hg
Boiling Point	159 to 160°C @ 10 mm Hg
Vapor Pressure	0.003 mmHg @ 25 °C
Flash Point TCC Value	117.2 °C TCC
logP (o/w)	3.481 est
Solubility
alcohol	Yes
acetone	Yes
ether	Yes
acetic acid	Yes
water, 27.68 mg/L @ 25 °C (est)	Yes
water	No

Organoleptic Properties

Odor Type: Herbal
parsley, herbal
Odor strength	low
General comment	At 100.00 %. parsley faint

Occurrences

Safety Information

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:
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

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.

Safety references

EPI System: View

AIDS Citations:Search

Cancer Citations:Search

Toxicology Citations: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