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

safrole
benzodioxole, 5-(2-propenyl)-

Sponsors

Name:5-prop-2-enyl-1,3-benzodioxole
CAS Number: 94-59-7Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:202-345-4
FDA UNII:RSB34337V9
Nikkaji Web:J3.946B
MDL:MFCD00005841
XlogP3:3.00 (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
Perfumer and Flavorist:Search
Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
JECFA Food Flavoring:1792 safrole
FDA Mainterm: SAFROLE--PROHIBITED
FDA Regulation:
FDA PART 189 -- SUBSTANCES PROHIBITED FROM USE IN HUMAN FOOD
Subpart C--Substances Generally Prohibited From Direct Addition or Use as Human Food
Sec. 189.180 Safrole.
 
Physical Properties:
Appearance:colorless to pale yellow clear liquid (est)
Assay: 98.00 to 100.00
Food Chemicals Codex Listed: No
Specific Gravity:1.07000 to 1.10000 @ 25.00 °C.
Pounds per Gallon - (est).: 8.903 to 9.153
Refractive Index:1.52700 to 1.53800 @ 20.00 °C.
Melting Point: 10.50 to 11.50 °C. @ 760.00 mm Hg
Boiling Point: 232.00 to 234.00 °C. @ 760.00 mm Hg
Boiling Point: 143.00 to 144.00 °C. @ 50.00 mm Hg
Congealing Point:10.30 °C.
Vapor Pressure:0.087000 mm/Hg @ 25.00 °C. (est)
Flash Point: 208.00 °F. TCC ( 97.78 °C. )
logP (o/w): 3.098 (est)
Soluble in:
 alcohol
 water, 75.98 mg/L @ 25 °C (est)
Insoluble in:
 water
Stability:
 non-discoloring in most media
 
Organoleptic Properties:
Odor Type: spicy
Odor Strength:medium ,
recommend smelling in a 10.00 % solution or less
Substantivity:44 hour(s) at 100.00 %
sweet warm spicy woody floral sassafrass anise
Odor Description:at 10.00 % in dipropylene glycol. sweet warm spicy woody floral sassafrass anise
Luebke, William tgsc, (1982)
Odor sample from: Berje Inc.
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
CosIng:cosmetic data
Cosmetic Uses: not used anymore
 
Suppliers:
Berjé
Safrole
Happening at Berje
BOC Sciences
For experimental / research use only.
Safrole
Fleurchem
safrole
Penta International
SAFROLE, Kosher
Reincke & Fichtner
Safrole
Synerzine
Safrole
 
Safety Information:
European information :
Most important hazard(s):
T - Toxic.
R 20/21/22 - Harmful by inhalation, in contact with skin and if swallowed.
R 45 - May cause cancer.
R 46 - May cause heritable genetic damage.
S 01/02 - Keep locked up and out of the reach of children.
S 20/21 - When using do not eat, drink or smoke.
S 23 - Do not breath vapour.
S 24/25 - Avoid contact with skin and eyes.
S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S 27 - Take off immediately all contaminated clothing.
S 28 - After contact with skin, wash immediately with plenty of water.
S 29 - Do not empty into drains.
S 36/37/39 - Wear suitable clothing, gloves and eye/face protection.
S 45 - In case of accident or if you feel unwell seek medical advice immediately.
S 53 - Avoid exposure - obtain special instructions before use.
 
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-rat LD50 1950 mg/kg
BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Toxicology and Applied Pharmacology. Vol. 7, Pg. 18, 1965.

oral-mouse LD50 2350 mg/kg
BEHAVIORAL: ATAXIA BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Food and Cosmetics Toxicology. Vol. 2, Pg. 327, 1964.

oral-rabbit LD50 1000 mg/kg
BEHAVIORAL: ATAXIA PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE KIDNEY, URETER, AND BLADDER: OTHER CHANGES IN URINE COMPOSITION
Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 35, Pg. 342, 1895.

intravenous-rabbit LD50 200 mg/kg
VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION VASCULAR: BP ELEVATION NOT CHARACTERIZED IN AUTONOMIC SECTION
Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 35, Pg. 342, 1895.

Dermal Toxicity:
skin-rabbit LD50 > 5000 mg/kg
Food and Cosmetics Toxicology. Vol. 12, Pg. 983, 1974.

subcutaneous-mouse LD50 1020 mg/kg
BEHAVIORAL: EXCITEMENT
Sapporo Igaku Zasshi. Sapporo Medical Journal. Vol. 3, Pg. 73, 1952.

subcutaneous-rabbit LDLo 1000 mg/kg
BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE
Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 35, Pg. 342, 1895.

Inhalation Toxicity:
Not determined
 
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 safrole usage levels up to:
 PROHIBITED: Should not be used as a fragrance ingredient.
 
Recommendation for safrole flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
NLM Hazardous Substances Data Bank:Search
Chemical Carcinogenesis Research Information System:Search
Cancer Citations:Search
Toxicology Citations:Search
Carcinogenic Potency Database:Search
EPA GENetic TOXicology:Search
Env. Mutagen Info. Center:Search
NLM Developmental and Reproductive Toxicity:Search
EPA Substance Registry Services (TSCA):94-59-7
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :5144
National Institute of Allergy and Infectious Diseases:Data
SCCNFP:opinion
WISER:UN 3082
WGK Germany:3
5-prop-2-enyl-1,3-benzodioxole
Chemidplus:0000094597
EPA/NOAA CAMEO:hazardous materials
RTECS:CY2800000 for cas# 94-59-7
 
References:
 5-prop-2-enyl-1,3-benzodioxole
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:94-59-7
Pubchem (cid):5144
Pubchem (sid):134971292
Flavornet:94-59-7
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 Everything Added to Food in the United States (EAFUS):View
CHEBI:View
CHEMBL:View
KEGG (GenomeNet):C10490
HMDB (The Human Metabolome Database):HMDB33591
FooDB:FDB011672
Export Tariff Code:2932.94.0000
Haz-Map:View
Typical G.C.
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
RSC Learn Chemistry:View
Formulations/Preparations:
•constituent of several essential oils, notably sassafras in which it is present to the extent of about 75%. •grade: technical
 
Potential Blenders and core components note
For Odor
spicy
cinnamaldehyde
FL/FR
For Flavor
spicy
cinnamaldehyde
FL/FR
 
Potential Uses:
FLbeer birch beer
FLcinnamon
FLgooseberry
FRnutmeg
FLroot beer
FLsarsaparilla
FLsassafras
 witch hazel
FRwormseed oil replacer
 
Occurrence (nature, food, other):note
 anise oil
Search Trop Picture
 anise seed oil star china @ 0.14%
Data GC Search Trop Picture
 anise star anise fruit
Search Trop Picture
 ayou wood oil @ 0.50%
Data GC Search Trop Picture
 basil plant
Search Trop Picture
 betel leaf oil @ 6.45%
Data GC Search Trop Picture
 cabocla flower oil brazil @ 1.00%
Data GC Search Trop Picture
 cassia plant
Search Trop Picture
 champaca concrete @ trace%
Data GC Search Trop Picture
 cinnamon ceylon cinnamon bark
Search Trop Picture
 cinnamon ceylon cinnamon bark oil
Search Trop Picture
 cinnamon ceylon cinnamon leaf
Search Trop Picture
 cinnamon ceylon cinnamon leaf oil
Search Trop Picture
 cinnamon ceylon cinnamon root bark
Search Trop Picture
 cinnamon ceylon cinnamon stem bark
Search Trop Picture
 cinnamon oil CO2 extract @ 0.00-0.02%
Data GC Search Trop Picture
 cubeb oil @ 0.08%
Data GC Search Trop Picture
 dill plant
Search Trop Picture
 dill seed oil
Search Trop Picture
 ho leaf oil @ 0.88%
Data GC Search Trop Picture
 mace oil @ 0.70%
Data GC Search Trop Picture
 mace oil CO2 extract @ 0.20%
Data GC Search Trop Picture
 michelia champaca flower absolute @ 0.51%
Data GC Search Trop Picture
 myristica fragrans fruit oil @ 2.80%
Data GC Search Trop Picture
 nutmeg
Search Trop Picture
 nutmeg extract CO2 west indian @ 0.10%
Data GC Search Trop Picture
 nutmeg oil
Search Trop Picture
 nutmeg oil hydrodistilled india @ 2.8%
Data GC Search Trop Picture
 nutmeg seed
Search Trop Picture
 nutmeg seed oil
Search Trop Picture
 osmanthus absolute @ 0.02%
Data GC Search Trop Picture
 pepper black pepper fruit
Search Trop Picture
 pepper black pepper fruit oil
Search Trop Picture
 pepper black pepper seed oil
Search Trop Picture
 petitgrain combava oil @ 0.24%
Data GC Search Picture
 phoebe oil brazil @ 0.70%
Data GC Search Trop Picture
 rosemary plant
Search Trop Picture
 sassafras
Search Trop Picture
 tamarind fruit
Search Trop Picture
 tamarind seed
Search Trop Picture
 tea leaf
Search Trop Picture
 zanthoxylum ovalifolium l. leaf oil australia @ 1.20%
Data GC Search Trop Picture
 
Synonyms:
 allyl catechol methylene ether
 allyl dioxybenzene methylene ether
meta-allyl pyrocatechin methylene ether
m-allyl pyrocatechinmethylene ether
4-allyl pyrocatechol formaldehyde acetal
 allyl pyrocatechol methylene ether
3-allyl-1,2-(methylenedioxy)benzene
4-allyl-1,2-methylene dioxybenzene
4-allyl-1,2-methylenedioxybenzene
5-allyl-1,3-benzodioxole
1-allyl-3,4-methylene dioxybenzene
1-allyl-3,4-methylenedioxybenzene
4-allyl-procatecol
5-allylbenzo[d][1,3]dioxole
4-allylcatechol methylene ether
m-allylpyrocatechin methylene ether
4-allylpyrocatechol formaldehyde acetal
4-allylpyrocatechol methylene ether
1,3-benzodioxole, 5-(2-propen-1-yl)-
 benzodioxole, 5-(2-propenyl)-
1,3-benzodioxole, 5-(2-propenyl)-
1,2-methylene dioxy-4-allyl benzene
1,2-methylenedioxy-4-allylbenzene
3,4-methylenedioxy-allylbenzene
3-[(3,4-methylenedioxy)phenyl]-1-propene
5-(prop-2-en-1-yl)-1,3-benzodioxole
5-prop-2-enyl-1,3-benzodioxole
5-(2-propenyl)-1,3-benzodioxole
 rhyuno
 shikimol
 shikomol
 
 
Notes:
constituent of several essential oils, notably sassafras. it has been used as a topical antiseptic and it is carcinogenic to the liver so it is no longer used as a flavoring agent in foods. Occurs in nutmeg. Banned by FDA for use in food. Formerly used as a food flavour 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.
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