dillapiol (dill)
1-allyl-2,3-dimethoxy-4,5-(methylenedioxy)benzene
 
Notes:
isolated from perilla frutenscens. Constit. of Japanese, Indian (Anethum sowa) and European (Anethum graveolens) dill oils and Piper spp. Also from seeds of Bunium persicum (black caraway) Dillapiole is an organic chemical compound and essential oil commonly extracted from dill weed, though can be found in a variety of other plants.
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      Product(s):
      484-31-1 Dillapiole
       
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CAS Number: 484-31-1Picture of molecule3D/inchi
FDA UNII: 438CJQ562D
Nikkaji Web: J12.531H
Beilstein Number: 0196037
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
 
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
Google Patents: Search
US Patents: Search
EU Patents: Search
Pubchem Patents: Search
PubMed: Search
NCBI: Search
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Physical Properties:
Appearance: colorless viscous liquid (est)
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Specific Gravity: 1.16440 @  0.00 °C.
Refractive Index: 1.53050 @  0.00 °C.
Melting Point: 28.00 to  29.00 °C. @ 760.00 mm Hg
Boiling Point: 285.00 to  292.00 °C. @ 760.00 mm Hg
Boiling Point: 160.00 to  161.00 °C. @ 10.00 mm Hg
Vapor Pressure: 0.006000 mmHg @ 25.00 °C. (est)
Flash Point: 222.00 °F. TCC ( 105.70 °C. ) (est)
logP (o/w): 2.343 (est)
Soluble in:
 alcohol
 water, 27.68 mg/L @ 25 °C (est)
Insoluble in:
 water
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Organoleptic Properties:
 
Odor Type: woody
 
 woody  spicy  
Odor Description:
wood spice
 
Odor and/or flavor descriptions from others (if found).
 
 
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Cosmetic Information:
None found
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Suppliers:
BOC Sciences
For experimental / research use only.
Dillapiole
ExtraSynthese
For experimental / research use only.
Dillapiole (GC) ≥99%
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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:
oral-mouse LD50  1000 mg/kg
Indian Journal of Pharmacy. Vol. 34, Pg. 69, 1972.

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
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Safety in Use Information:
Category: natural substances and extractives
Recommendation for dillapiol (dill) usage levels up to:
 not for fragrance use.
 
Recommendation for dillapiol (dill) flavor usage levels up to:
 not for flavor use.
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Safety References:
EPI System: View
AIDS Citations: Search
Cancer Citations: Search
Toxicology Citations: Search
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 10231
National Institute of Allergy and Infectious Diseases: Data
 4,5-dimethoxy-6-prop-2-enyl-1,3-benzodioxole
Chemidplus: 0000484311
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References:
 4,5-dimethoxy-6-prop-2-enyl-1,3-benzodioxole
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 10231
Pubchem (sid): 134975341
Flavornet: 484-31-1
Pherobase: View
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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): C10449
HMDB (The Human Metabolome Database): HMDB30725
FooDB: FDB002649
Typical G.C.
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
Wikipedia: View
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
None Found
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Occurrence (nature, food, other): note
 coriander seed oil
Search Trop  Picture
 coriander seed oil cuba @ 0.45%
Data  GC  Search Trop  Picture
 crithmum maritimum oil @ <0.10%
Data  GC  Search Trop  Picture
 cubeb oil @ 0.16%
Data  GC  Search Trop  Picture
 cumin seed
Search Trop  Picture
 dill
Search Trop  Picture
 dill leaf
Search Trop  Picture
 dill leaf oil
Search Trop  Picture
 dill oil
Search Trop  Picture
 dill plant
Search Trop  Picture
 dill root oil
Search Trop  Picture
 dill seed
Search Trop  Picture
 dill shoot oil
Search Trop  Picture
 dill weed oil cuba @ 0.31%
Data  GC  Search Trop  Picture
 fennel root oil
Search Trop  Picture
 fennel sprout
Search Trop  Picture
 parsley fruit oil
Search Trop  Picture
 parsley seed oil
Search Trop  Picture
 pepper spiked pepper
Search Trop  Picture
 perilla
Search Trop  Picture
 piper marginatum
Search Trop  Picture
 salvia leucantha
Search Trop  Picture
 trachyspermum roxburghianum benth. ex. kurz. seed oil india @ 0.20%
Data  GC  Search Trop  Picture
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Synonyms:
1-allyl-2,3-dimethoxy-4,5-(methylene dioxy) benzene
1-allyl-2,3-dimethoxy-4,5-(methylenedioxy)benzene
6-allyl-4,5-dimethoxy-1,3-benzodioxol
 apiole (dill)
 benzene, 1-allyl-2,3-dimethoxy-4,5-(methylenedioxy)-
1,3-benzodioxole, 4,5-dimethoxy-6-(2-propen-1-yl)-
1,3-benzodioxole, 4,5-dimethoxy-6-(2-propenyl)-
 dill apiole (dill)
4,5-dimethoxy-6-(prop-2-en-1-yl)-1,3-benzodioxole
4,5-dimethoxy-6-prop-2-enyl-1,3-benzodioxole
4,5-dimethoxy-6-prop-2-enyl-2H-benzo[d]1,3-dioxolene
1,2-methylene dioxy-5,6-dimethoxy-4-allyl benzene
1,2-methylenedioxy-5,6-dimethoxy-4-allylbenzene
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Articles:
PubMed: [Chemical constituents of Osmanthus fragrans fruits].
PubMed: Dillapiol: a pyrethrum synergist for control of the Colorado potato beetle.
PubMed: Genetic toxicity of dillapiol and spinosad larvicides in somatic cells of Drosophila melanogaster.
PubMed: Chemical composition and antifungal activity of essential oils and supercritical CO2 extracts of Apium nodiflorum (L.) Lag.
PubMed: The volatile constituents of Salvia leucantha.
PubMed: HIV-1-inhibiting activity of the essential oil of Ridolfia segetum and Oenanthe crocata.
PubMed: Bioactivities of Piper aduncum L. and Piper obliquum Ruiz & Pavon (Piperaceae) essential oils from Eastern Ecuador.
PubMed: Potential control of Aedes aegypti (Diptera: Culicidae) with Piper aduncum L. (Piperaceae) extracts demonstrated by chromosomal biomarkers and toxic effects on interphase nuclei.
PubMed: A synthetic derivative of plant allylpolyalkoxybenzenes induces selective loss of motile cilia in sea urchin embryos.
PubMed: Ciliogenesis, ciliary function, and selective isolation.
PubMed: Modulation of human cytochrome P450 3A4 (CYP3A4) and P-glycoprotein (P-gp) in Caco-2 cell monolayers by selected commercial-source milk thistle and goldenseal products.
PubMed: Dillapiol and Apiol as specific inhibitors of the biosynthesis of aflatoxin G1 in Aspergillus parasiticus.
PubMed: Phytochemistry and antifungal properties of the newly discovered tree Pleodendron costaricense.
PubMed: Evaluation of the efficacy of dill apiol and pyriproxyfen in the treatment and control of Xenopsylla cheopis flea Roths (Siphonaptera: Pulicidae).
PubMed: Traditionally-used antimalarials from the Meliaceae.
PubMed: Antimicrobial constituents of Foeniculum vulgare.
PubMed: An in vitro evaluation of human cytochrome P450 3A4 inhibition by selected commercial herbal extracts and tinctures.
PubMed: Evaluation of anti-inflammatory-related activity of essential oils from the leaves and resin of species of Protium.
PubMed: Genetic analysis of nothoapiol formation in Perilla frutescens.
PubMed: Insecticidal defenses of Piperaceae from the neotropics.
PubMed: Five new prenylated p-hydroxybenzoic acid derivatives with antimicrobial and molluscicidal activity from Piper aduncum leaves.
PubMed: Isolation of dillapiol from a chemotype of Perilla frutescens as an active principle for prolonging hexobarbital-induced sleep.
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