Safrole
- CAS No.
- 94-59-7
- Chemical Name:
- Safrole
- Synonyms
- SAFROL;5-ALLYL-1,3-BENZODIOXOLE;3,4-Methylenedioxy-allybenzene;Benzene, 1,2-methylenedioxy-4-allyl-;SAFROLE;Safrene;SAFROLR;Shikomol;shikimol;rhyunooil
- CBNumber:
- CB4365927
- Molecular Formula:
- C10H10O2
- Molecular Weight:
- 162.19
- MOL File:
- 94-59-7.mol
- Modify Date:
- 2023/11/28 16:31:44
| Melting point | 11.2 °C(lit.) |
|---|---|
| Boiling point | 232-234 °C(lit.) |
| Density | 1.099 g/mL at 20 °C |
| vapor pressure | 1 mm Hg ( 63.8 °C) |
| refractive index |
n |
| Flash point | 208 °F |
| storage temp. | 2-8°C |
| solubility | DMF: 20 mg/ml; DMSO: 25 mg/ml; Ethanol: 33 mg/ml; Ethanol:PBS(pH 7.2) (1:1): 0.5 mg/ml |
| color | yellow |
| Odor | at 10.00 % in dipropylene glycol. sweet warm spicy woody floral sassafrass anise |
| Odor Type | spicy |
| Water Solubility | insoluble, <0.1 g/100 mL at 18 ºC |
| Merck | 13,8395 |
| BRN | 136380 |
| Dielectric constant | 3.1（21℃） |
| Stability | Stable. Combustible. Incompatible with strong oxidizing agents. |
| LogP | 3.098 (est) |
| CAS DataBase Reference | 94-59-7(CAS DataBase Reference) |
| IARC | 2B (Vol. 10, Sup 7) 1987 |
| NIST Chemistry Reference | 1,3-Benzodioxole, 5-(2-propenyl)-(94-59-7) |
| EPA Substance Registry System | Safrole (94-59-7) |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |   GHS07,GHS08 |
|||||||||
|---|---|---|---|---|---|---|---|---|---|---|
| Signal word | Danger | |||||||||
| Hazard statements | H302-H315-H341-H350 | |||||||||
| Precautionary statements | P202-P264-P270-P301+P312-P302+P352-P308+P313 | |||||||||
| Hazard Codes | T | |||||||||
| Risk Statements | 45-22-68 | |||||||||
| Safety Statements | 53-45 | |||||||||
| RIDADR | UN 3082 9/PG 3 | |||||||||
| WGK Germany | 3 | |||||||||
| RTECS | CY2800000 | |||||||||
| HS Code | 29329400 | |||||||||
| Toxicity | LD50 in rats, mice (mg/kg): 1950, 2350 orally (Hagan) | |||||||||
| NFPA 704 |
|
Safrole Chemical Properties,Uses,Production
Description
In the early 1990s, certain forest shrubs of the Piperaceae, indigenous to the humid forests of Central America and Greater Amazonia, were found to contain high levels of safrole in their leaves. The Brazilian Amazon contains a wide variety of Piper species but attention had focused on P. hispidinervum and P. callosum, two species with high safrole content. Subsequently, P. callosum has been dropped in the research work in favor of the more promising P. hispidinervum. The essential oil of P. hispidinervum contains high levels (83–93%) of safrole in leaves, which can be easily extracted by hydrodistillation.
Chemical Properties
Safrole is a colorless to yellow liquid with an odor of camphor or sassafras.
Occurrence
Originally isolated in the oil from roots of Sassafras officinale; constituent of several essential oils, such as camphor, nutmeg and cinnamon leaves; the essential oil from the roots of Nemuaron humboldtii contains up to 99% safrole; Brazilian sassafras oil, up to 93%; and American sassafras oil, up to 80%. Also reported found in banana, cinnamon bark and leaf, nutmeg, mace, tamarind, pepper, cocoa, coriander seed, dill herb, dried bonito, lemon balm, ashanti pepper and green maté.
Uses
Safrole, the main component of oil of sassafras, is widely used as a flavoring agent in drugs and in the manufacture of heliotropin, perfumes, soaps, and piperonyl butoxide (a compound used in a variety of insecticides to enhance the pesticidal properties of other active ingredients). Safrole has also been used as a preservative in mucilage and library paste and as a flotation frother. Oil of sassafras, which contains safrole, was formerly used to flavor some soft drinks, such as root beer. However, this was banned in the United States in 1960. Safrole has also been used in the illicit production of the drug 3,4- methylenedioxymethamphetamine (MDMA or ecstasy) and the US Drug Enforcement Administration has designated safrole a List I Chemical.
Preparation
By distillation and/or freezing of such oils as Cinnamomum micranthum, Octea cymharum and oil of sassafras.
Definition
ChEBI: A member of the class of benzodioxoles that is 1,3-benzodioxole which is substituted by an allyl group at position 5. It is found in several plants, including black pepper, cinnamon and nutmeg, and is present in several essential oils, notably that of sass fras. It has insecticidal properties and has been used as a topical antiseptic. Although not thought to pose a significant carcinogenic risk to humans, findings of weak carcinogenicity in rats have resulted in the banning of its (previously widespread) use in perfumes and soaps, and as a food additive.
General Description
Clear colorless or slightly yellow liquid with the odor of sassafras. Denser than water (density 1.09 g / cm3) and insoluble in water. Hence sinks in water. Obtained from oil of sassafras or oil of camphor.
Air & Water Reactions
Insoluble in water.
Reactivity Profile
Safrole, an acetal, is readily hydrolyzed in acidic solution to give 4-allylpyrocatechol and formaldehyde (or formaldehyde polymers).
Hazard
Toxic by ingestion, may not be used in food products (FDA), a possible carcinogen.
Fire Hazard
Safrole is combustible.
Toxicology
Safrole is a colorless oily liquid possessing a sweet, warm-spicy flavor. It has been used as a flavoring agent for more than 60 years. Oil of sassafras, which contains 80% safrole, also has been used as a spice. In the United States, the FDA banned the use of safrole in 1958 and many other countries followed this lead and also banned the use of safrole in flavors. Safrole, either naturally occurring in sassafras oil or the synthetic chemical, has been shown to induce liver tumors in rats. The continuous administration of safrole at 5,000 ppm in the total diet of rats caused liver tumors. Studies in dogs showed extensive liver damage at 80 and 40 mg/kg, lesser damage at lower levels, but no tumors. In vivo, safrole metabolites into 1’-hydroxysafrole. The structures of safrole and 1’-hydroxysafrole are shown in Figure 10.14.
Safety Profile
Confirmed carcinogen with experimental carcinogenic and neoplastigenic data. Poison by intravenous route. Moderately toxic by ingestion and subcutaneous routes. Experimental reproductive effects. Human mutation data reported. A sktn irritant. Combustible when exposed to heat or flame. When heated to decomposition it emits acrid smoke and irritating fumes. See also ALDEHYDES and ALLYL COMPOUNDS.
Potential Exposure
This compound has been used to flavor beverages and foods. It is also reported to be used in soap manufacture, perfumery, sleep aids, sedatives, and pesticides. The FDA estimated exposure to safrole of the general public through food consumption was extremely low since the Agency prohibited its used in food. Derived from oil of sassafras or camphor. Minimal exposure may occur through the use of edible spices, including nutmeg and mace, which contain low levels of naturally occurring safrole.
Carcinogenicity
Safrole is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in experimental animals.
Metabolism
Rats and guinea-pigs, dosed orally or ip with safrole, excreted in the urine 3-N,N-dimethylamino-1 -(3',4'-methylenedioxyphenyl)-1 -propanone (Oswald, Fishbein, Corbett & Walker, 1971). In addition, the rats excreted in the urine a major metabolite,3-piperidyl-l-(3',4'-methylenedioxyphenyl)-l-propanone, and traces of 3-pyrrolidinyl-l-(3',4'-methylenedioxyphenyl)-l-propanone. All three aminoketones decomposed to form 1-(3',4-methylenedioxyphenyl)-3-propen-l-one. Two metabolites formed by the epoxide-diol pathway and excreted in the urine of rats and guinea-pigs dosed with safrole were identified as l,2-methylenedioxy-4-(2',3'-dihydroxypropyl)benzene and l,2-dihydroxy-4-(2',3'-dihydroxypropyl)benzene (Horning, Bell, Carman & Stillwell, 1974).
Shipping
Environmentally hazardous substances, liquid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous hazardous material, Technical Name Required.
Purification Methods
Safrole has been purified by fractional distillation, although it has also been recrystallised from low boiling pet ether at low temperatures. [IR: Briggs et al. Anal Chem 29 904 1957, UV: Patterson & Hibbert J Am Chem Soc 65 1962 1943.] The maleic anhydride adduct forms yellow crystals from toluene m 257o [Hickey J Org Chem 13 443 1948], and the picrate forms orange-red crystals from CHCl3 [Baril & Magrdichian J Am Chem Soc 58 1415 1936]. [Beilstein 19 H 39, 19 I 617, 19 II 29, 19 III/IV 275, 19/1 V 553.]
Incompatibilities
Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explo- sions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides. Safrole, an acetal, is read- ily hydrolyzed in acidic solution to give 4-allylpyrocatechol and formaldehyde (or formaldehyde polymers)
Waste Disposal
Consult with environmental regulatory agencies for guidance on acceptable disposal practices. Generators of waste containing this contaminant (≥100 kg/mo) must conform to EPA regulations governing storage, transportation, treatment, and waste disposal. In accordance with 40CFR165, follow recommendations for the disposal of pesticides and pesticide containers. Must be disposed properly by following package label directions or by contacting your local or federal environmental control agency, or by contacting your regional EPA office.
Safrole Preparation Products And Raw materials
Raw materials
1of2
chevron_rightPreparation Products
1of2
chevron_right