isosafrole
1,3-benzodioxole, 5-[(1E)-1-propen-1-yl]-
 
Notes:
Isol. from leaves of the curryleaf (Murraya koenigii) and from star anise oil (Illicium religiosum) It is a precursor in the synthesis of the insecticide synergist piperonyl butoxide and the recreational drug MDMA ("Ecstacy."); Safrole is a natural plant constituent, found in oil of sassafras and certain other essential oils. It is a member of the methylenedioxybenzene group of compounds, many of which (e.g. piperonyl butoxide) are extensively used as insecticide synergists. A major source of human exposure to safrole is through consumption of spices, such as nutmeg, cinnamon and black pepper, in which safrole is a constituent. Safrole is also present in root beer, and has been used as an additive in chewing gum, toothpaste, soaps and certain pharmaceutical preparations. Safrole is a weak hepatocarcinogen and it is a matter of considerable interest whether the ally1 moiety or the methylenedioxy group, or both, are involved in the mechanism of its carcinogenesis. Safrole is extensively metabolized, giving rise to a large number of metabolites. Metabolism involves essentially two major routes, oxidation of the ally1 side chain, and oxidation of the methylenedioxy group with subsequent cleavage to form the catechol. Safrole undergoes oxidation of the allylic group to yield the 2, 3-epoxide (safrole epoxide). The dihydrodiol is one of the metabolites of safrole, and presumably arises from the hydration of the 2, 3-epoxide. The principal route of metabolism of safrole is through cleavage of the methylenedioxy group, the major metabolites being allylcatechol and its isomer, propenylcatechol. Eugenol and its isomer I-methoxy- 2-hydroxy-4-allylbenzene have been detected as minor metabolites in the rat, mouse and man. (PMID: 6719936); Safrole, also known as shikimol, is a colorless or slightly yellow oily liquid. It is typically extracted from the root-bark or the fruit of sassafras plants in the form of sassafras oil, or synthesized from other related methylenedioxy compounds. It is the principal component of brown camphor oil, and is found in small amounts in a wide variety of plants, where it functions as a natural pesticide. The Ocotea cymbarum[verification needed] oil made of the Ocotea pretiosa[verification needed], a plant growing in Brazil, and sassafras oil made of Sassafras albidum, a tree growing in eastern North America, are the main natural sources for safrole. It has a characteristic "candy-shop" aroma.
  • Penta International
    • Penta International Corporation
      Chemistry innovation
      At Penta, our products and services help businesses do business better.
      For over 30 years, Penta Manufacturing Company has played a growing role in worldwide chemistry innovations and applications. As an industry leader, Penta continues to pioneer chemistry-based solutions for practically every area of commerce. Our products and expertise have helped fuel technical advances in dozens of commercial applications including flavoring, coloring, fragrances and chemical processes.
      US Email: Technical Services
      US Email: Sales
      US Voice: (973) 740-2300
      US Fax: (973) 740-1839
      Product(s):
      09-63000 ISOSAFROLE
       
Synonyms   Articles   Notes   Search
5-[(E)-prop-1-enyl]-1,3-benzodioxole (Click)
CAS Number: 120-58-1Picture of molecule
Other: 191281-03-5
ECHA EINECS - REACH Pre-Reg: 204-410-2
FDA UNII: W6337429LF
Nikkaji Web: J5.328G
Beilstein Number: 0082640
MDL: MFCD00005838
XlogP3: 3.10 (est)
Molecular Weight: 162.18810000
Formula: C10 H10 O2
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
IBM Patents: Obtain
Pubchem Patents: Search
PubMed: Search
NCBI: Search
Synonyms   Articles   Notes   Search   Top
Physical Properties:
Appearance: colorless to pale yellow clear liquid (est)
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Melting Point: 6.75 °C. @ 760.00 mm Hg
Boiling Point: 127.00 to  128.00 °C. @ 15.00 mm Hg
Boiling Point: 254.00 to  255.00 °C. @ 760.00 mm Hg
Vapor Pressure: 0.025000 mm/Hg (est)
Flash Point: 230.00 °F. TCC ( 110.10 °C. ) (est)
logP (o/w): 3.344 (est)
Soluble in:
 alcohol
 water, 88.68 mg/L @ 25 °C (est)
Insoluble in:
 water
Synonyms   Articles   Notes   Search   Top
Organoleptic Properties:
Odor Type: spicy
Odor Strength: medium ,
recommend smelling in a 10.00 % solution or less
 sweet  sassafrass  spicy  
Odor Description:
at 10.00 % in dipropylene glycol. 
sweet sassafrass spicy
  
Synonyms   Articles   Notes   Search   Top
Cosmetic Information:
None found
Synonyms   Articles   Notes   Search   Top
Suppliers:
Penta International
ISOSAFROLE
Reincke & Fichtner
isoSafrole
Sigma-Aldrich: Aldrich
For experimental / research use only.
isoSafrole mixture of cis and trans
Synonyms   Articles   Notes   Search   Top
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.
Human Experience:
8 % solution: no irritation or sensitization.
Oral/Parenteral Toxicity:
intraperitoneal-mouse LD50  324 mg/kg
Yakugaku Zasshi. Journal of Pharmacy. Vol. 104, Pg. 793, 1984.

oral-mouse LD50  2470 mg/kg
BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: ATAXIA
Food and Cosmetics Toxicology. Vol. 2, Pg. 327, 1964.

intravenous-rabbit LDLo  300 mg/kg
Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 35, Pg. 342, 1895.

oral-rat LD50  1340 mg/kg
Toxicology and Applied Pharmacology. Vol. 7, Pg. 18, 1965.

Dermal Toxicity:
subcutaneous-mouse LD50 1030 mg/kg
BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Sapporo Igaku Zasshi. Sapporo Medical Journal. Vol. 3, Pg. 73, 1952.

Inhalation Toxicity:
Not determined
Synonyms   Articles   Notes   Search   Top
Safety in Use Information:
Category: natural substances and extractives
IFRA fragrance material specification:
 Safrole as such should not be used as a fragrance ingredient; essential oils containing safrole should not be used at a level such that the total concentration of safrole exceeds 0.01% in consumer products. Examples of essential oils with a high safrole content are Sassafras oil (Sassafras officinale Nees& Eberm.), Ocotea Cymbarum oil (Ocotea pretiosa Metz) and certain qualities of Camphor oils. The total concentration of safrole, isosafrole and dihydrosafrole should not exceed 0.01% in consumer products. These recommendations are based on the conclusions of the Scientific Committee on Cosmetology of the EEC on safrole and on the similarity of the biological activity of these substances (Scientific Committee of Cosmetology of the EEC, opinion reached on September 2, 1980; Communication to the EEC Commission ENV/521/79 and IARC Monograph Vol. 10, 1976, 231-244).
IFRA: View Standard
limits in the finished product for - "leave on the skin contact":
  0.0100 % Restriction.
limits in the finished product for - "wash off the skin contact":
  0.0100 % Restriction.
limits in the finished product for - "no skin contact":
  0.0100 % Restriction.
Recommendation for isosafrole usage levels up to:
 PROHIBITED: Should not be used as a fragrance ingredient.
 
Recommendation for isosafrole flavor usage levels up to:
 not for flavor use.
Synonyms   Articles   Notes   Search   Top
Safety References:
EPI System: View
NLM Hazardous Substances Data Bank: Search
Chemical Carcinogenesis Research Information System: Search
Cancer Citations: Search
Toxicology Citations: Search
EPA GENetic TOXicology: Search
Env. Mutagen Info. Center: Search
EPA Substance Registry Services (TSCA): 120-58-1
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 637796
National Institute of Allergy and Infectious Diseases: Data
WGK Germany: 3
 5-[(E)-prop-1-enyl]-1,3-benzodioxole
Chemidplus: 0000120581
EPA/NOAA CAMEO: hazardous materials
RTECS: DA5950000 for cas# 120-58-1
Synonyms   Articles   Notes   Search   Top
References:
 5-[(E)-prop-1-enyl]-1,3-benzodioxole
NIST Chemistry WebBook: Search Inchi
Canada Domestic Sub. List: 120-58-1
Pubchem (cid): 637796
Pubchem (sid): 134975200
Synonyms   Articles   Notes   Search   Top
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): C10472
HMDB (The Human Metabolome Database): HMDB02333
FooDB: FDB012296
Export Tariff Code: 2932.91.0000
Haz-Map: View
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
Wikipedia: View
RSC Learn Chemistry: View
Synonyms   Articles   Notes   Search   Top
Potential Blenders and core components note
 
None Found
 
Synonyms   Articles   Notes   Search   Top
Potential Uses:
 root beerFR
 sarsaparilla 
 sassafrasFR
Synonyms   Articles   Notes   Search   Top
Occurrence (nature, food, other): note
 curry leaf
Search Trop  Picture
 illicium religiosum oil
Search Trop  Picture
Synonyms   Articles   Notes   Search   Top
Synonyms:
1,3-benzodioxole, 5-[(1E)-1-propen-1-yl]-
(E)-5-(prop-1-en-1-yl)benzo[d][1,3]dioxole
5-[(1E)-prop-1-en-1-yl]-1,3-benzodioxole
5-[(1E)-prop-1-en-1-yl]-2H-1,3-benzodioxole
5-prop-1-enyl-1,3-benzodioxole
5-[(E)-prop-1-enyl]-1,3-benzodioxole
5-[(1E)-1-propen-1-yl]-1,3-benzodioxole
((E)-5-propenyl)-benzo[1,3]dioxole
Synonyms   Articles   Notes   Search   Top
Synonyms   Articles   Notes   Search   Top
Please share your Comments.
Email Address:
 
 
 
 
Top of Page Home
Copyright © 1980-2017 The Good Scents Company (tgsc) ™ Disclaimer Privacy Policy