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Safrole

Overview and history Physiochemical properties Synthesis Application Warning and risk References
Safrole
Safrole
CAS No.
94-59-7
Chemical Name:
Safrole
Synonyms
SAFROL;SAFROLE;Safrene;Shikomol;shikimol;rhyunooil;safrolemf;Shikimole;NSC 11831;Rhyuno oil
CBNumber:
CB4365927
Molecular Formula:
C10H10O2
Formula Weight:
162.19
MOL File:
94-59-7.mol

Safrole Properties

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 
n20/D 1.537(lit.)
Flash point:
208 °F
color 
yellow
Water Solubility 
insoluble, <0.1 g/100 mL at 18 ºC
Merck 
13,8395
Stability:
Stable. Combustible. Incompatible with strong oxidizing agents.
CAS DataBase Reference
94-59-7(CAS DataBase Reference)
NIST Chemistry Reference
1,3-Benzodioxole, 5-(2-propenyl)-(94-59-7)
EPA Substance Registry System
1,3-Benzodioxole, 5-(2-propenyl)-(94-59-7)

SAFETY

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
Hazardous Substances Data 94-59-7(Hazardous Substances Data)
Toxicity LD50 in rats, mice (mg/kg): 1950, 2350 orally (Hagan)

Safrole price More Price(3)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Cayman Chemical 13894 Safrole ≥98% 94-59-7 10mg $75 2018-11-13 Buy
Cayman Chemical 13894 Safrole ≥98% 94-59-7 25mg $141 2018-11-13 Buy
Cayman Chemical 13894 Safrole ≥98% 94-59-7 50mg $263 2018-11-13 Buy

Safrole Chemical Properties,Uses,Production

Overview and history

Safrole is a phenylpropene that usually extracted from the root-bark or the fruit of sassafras plants in the form of sassafras oil or is synthesized from catechol or other related methylenedioxy-compounds[1]. It is the key component of brown camphor oil, and also exists in small amounts in a wide variety of plants, where it functions as a natural pesticide. The major source of safrole includes Ocotea cymbarum oil made from Ocotea pretiosa(a plant growing in Brazil), and sassafras oil made from Sassafras albidum(a tree growing in eastern North America)[2, 3].
Safrole is one of the natural components of refined oils in more than fifty kinds of vegetables[4]. Many of them can be made into seasonings and are one of the major components of essential oils, such as sassafras, camphor, nutmeg, black pepper, sweet basil, mace, cinnamon, anise and piper betle flower[4]. Safrole is a precursor chemical of ring-substituted amphetamine-type substances such as MDMA or Ecstasy, MDA, MDE[5]. Safrole and isosafrole(S-isomer of safrole) were once used extensively as a seasoning in soft drinks. For example, Sarsaparilla and Coke have used sassafras oil as seasoning, which contained nearly 85% safrole and isosafrole. Intake estimates of flavoring substances are generally very poor because of the lack of data on the concentrations of these chemicals naturally occurring or voluntarily added in foodstuffs. Within the Council of Europe, UK and France provided calculations based on their respective food consumption data and on concentration levels documented or assumed[6, 7].
Since safrole and isosafrole are carcinogens, adding sassafras oil in soft drinks has been prohibited in the US since 1970, while it was defined as a kind of food additive and treated as a special element of seasonings in the Republic of China with limited usage[8, 9].

Physiochemical properties

Safrole appears as a colorless or slightly yellow oily liquid. It has a characteristic "sweet-shop" aroma. As a naturally occurring substance, it is a derivative of the aromatic phenol ether 1,3-benzodioxole(HSDB 2009)[12]. It exists at room temperature as colorless or pale-yellow oil with an odor of sassafras. It is practically insoluble in water, insoluble in glycerine, slightly soluble in propylene glycol, soluble in alcohol, and miscible with chloroform and ether[11].

Synthesis

Safrole is produced by distillation of oils rich in safrole(such as sassafras, nutmeg, mace, cinnamon, anise, black pepper and sweet basil). It is nearly impossible to obtain large quantities of safrole and/or sassafras oil without arousing the suspicion of law enforcement, as Safrole is currently a List I chemical[12]. U.S. production of safrole was 257,000 lb in 1969 and 277,000 lb in 1970, but had fallen to 12,000 lb by 1977(HSDB 2009)[10]. In 2009, safrole was manufactured by only one facility worldwide, in the United States[SRI 2009][13], and was available from 11 U.S. suppliers(ChemSources 2009)[14]. U.S. imports of safrole were 36,000 lb in 1980(HSDB 2009)[10] and ranged from 11,000 to 132,000 lb in 1997, 2003, 2004, and 2005(USITC 2009)[15]. U.S. exports of safrole were 6,600 lb in 1996 and 35,200 lb in 1998.

Application

Safrole can be 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)(HSDB 2009)[10]. 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 use or any other addition of safrole or oil of sassafras to food was banned in the United States in 1960(IARC1976, HSDB 2009)[10, 16]. Safrole has also been used in the illicit production of the drug 3,4-methylenedioxymethamphetamine(MDMA, or ecstasy), and the U.S. Drug Enforcement Administration has designated safrole a List I Chemical(DEA 2009)[17].

Warning and risk

Safrole are carcinogens[7, 8], therefore, adding sassafras oil in soft drinks has been prohibited in the US since 1970, while it was defined as a kind of food additive and treated as a special element of seasonings in the Republic of China. However, it can be used only in soft drinks with the use limit below 1μg/mL, according to food additive regulations[18]. Safrole and isosafrole were once used extents have a connection with inductive liver tumors[19]. A high concentration(0.5%) of safrole and isosafrole has been shown to increase the occurrence rate of malignant tumors in mice Safrole or 4-allyl-l; 2-methylenedioxybenzene is a plant constituent that is a hepatotoxin for animals and man. The major toxicity of safrole and isosafrole come from their carcinogenic nature after oxidation. Safrole is oxidized into1-hydroxysafrole by many mammals and whose derivatives including isosafrole and dihydrosafrole, which are all both carcinogenic[20, 21].

References

  1. Perkin, William Henry & Trikojus, Victor Martin[1927]. "CCXII. —A synthesis of safrole and o-safrole". Journal of the Chemical Society: 1663–1666. doi:10.1039/JR9270001663. Retrieved 28 December 2013.
  2. Hickey, Michael J.[1948]. "Investigation of the chemical constituents of Brazilian sassafras oil". Journal of Organic Chemistry. 13[3]: 443–6.
  3. Kamdem, Donatien; Gage, Douglas[2007]. "Chemical Composition of Essential Oil from the Root Bark of Sassafras albidum". Planta Medica. 61[6]: 574–5.
  4. Choong Y M and Lin H J, 2000, A Rapid and Simple Gas chromatographic Method for Direct Determination of safrole in soft drinks, Journal of Food and Drug Analysis, vol. 9, No. 1, Pages: 27-32.
  5. Rianjanu, A., Roto, R., Julian, T., Hidayat, S. N., Kusumaatmaja, A., & Suyono, E. A., et al.[2018]. Polyacrylonitrile nanofiber-based quartz crystal microbalance for sensitive detection of safrole. Sensors, 18(4], 1150.
  6. https://ec.europa.eu/food/sites/food/files/safety/docs/fs_food-improvement-agents_flavourings-out116.pdf
  7. Borchert, Wislocki and Miller, 2012, The Metabolism of the Naturally Occurring Hepatocarcinogen,
  8. https://toxnet.nlm.nih.gov/cgi-bin/sis/search/a?dbs+hsdb:@term+@DOCNO+2653
  9. https://www.fda.gov.tw/tc/includes/GetFile.ashx?id=f636695477623841313
  10. HSDB. 2009. Hazardous Substances Data Bank. National Library of Medicine.
  11. Report on Carcinogens, 2011, Twelfth Edition, National Toxicology Program, Department of Health and Human Services, and Page 374.
  12. The Chemistry Encyclopedia,[2005] Safrole http://www.chemistrydaily.com/chemistry/Safrole
  13. SRI. 2009. Directory of Chemical Producers. Menlo Park, CA: SRI Consulting. Database edition. Last accessed: 7/14/09.
  14. ChemSources. 2009. Chem Sources - Chemical Search. Chemical Sources International.
  15. USITC. 2009. USITC Interactive Tariff and Trade DataWeb. United States International Trade Commission.
  16. IARC. 1976. Safrole, isosafrole, and dihydrosafrole. In Some Naturally Occurring Substances. IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Humans, vol. 10. Lyon, France: International Agency for Research on Cancer. pp. 231-244.
  17. DEA. 2009. Safrole and Sassafras Oil are used in the Illicit Manufacture of MDMA. Drug Enforcement Administration.
  18. https://www.sciencedirect.com/topics/agricultural-and-biological-sciences/sassafras
  19. Long, E. L., Nelson, A. A., Fitzhugh, O. G., & Hansen, W. H.[1963]. Liver tumours produced in rats by feeding safrole. Journal of the American Medical Association, 184, 159-159.
  20. Borchert, P, et al. "The metabolism of the naturally occurring hepatocarcinogen safrole to 1'-hydroxysafrole and the electrophilic reactivity of 1'-acetoxysafrole. " Cancer Research 33.3(1973]: 575-589.
  21. Borchert, P, et al. "1'-Hydroxysafrole, a proximate carcinogenic metabolite of safrole in the rat and mouse." Cancer Research 33.3(1973]:590-600.

Chemical Properties

light yellow-green liquid

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.

Uses

In perfumery; denaturing fats in soap manufacture; also in manufacture of heliotropin. Formerly as flavoring agent in foods, drugs and beverages.

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).

Fire Hazard

Safrole is combustible.

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.]

Safrole Preparation Products And Raw materials

Raw materials

Preparation Products


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94-59-7(Safrole)Related Search:


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  • Rcra waste number U203
  • rcrawastenumberu203
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