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Safrole information


Safrole[1]
Skeletal formula of safrole
Ball-and-stick model of safrole
Names
Preferred IUPAC name
5-(Prop-2-en-1-yl)-2H-1,3-benzodioxole
Other names
5-(2-Propenyl)-1,3-benzodioxole
5-Allylbenzo[d][1,3]dioxole
3,4-Methylenedioxyphenyl-2-propene
Identifiers
CAS Number
  • 94-59-7 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:8994 checkY
ChEMBL
  • ChEMBL242273 checkY
ChemSpider
  • 13848731 checkY
ECHA InfoCard 100.002.133 Edit this at Wikidata
EC Number
  • 202-345-4
KEGG
  • C10490 checkY
PubChem CID
  • 5144
RTECS number
  • CY2800000
UNII
  • RSB34337V9 checkY
UN number 3082
CompTox Dashboard (EPA)
  • DTXSID0021254 Edit this at Wikidata
InChI
  • InChI=1S/C10H10O2/c1-2-3-8-4-5-9-10(6-8)12-7-11-9/h2,4-6H,1,3,7H2 checkY
    Key: ZMQAAUBTXCXRIC-UHFFFAOYSA-N checkY
  • InChI=1/C10H10O2/c1-2-3-8-4-5-9-10(6-8)12-7-11-9/h2,4-6H,1,3,7H2
    Key: ZMQAAUBTXCXRIC-UHFFFAOYAD
SMILES
  • C=CCc1ccc2OCOc2c1
Properties
Chemical formula
C10H10O2
Molar mass 162.188 g·mol−1
Density 1.096 g/cm3
Melting point 11 °C (52 °F; 284 K)
Boiling point 232 to 234 °C (450 to 453 °F; 505 to 507 K)
Magnetic susceptibility (χ)
−97.5×10−6 cm3/mol
Hazards
GHS labelling:
Pictograms
GHS07: Exclamation markGHS08: Health hazard
Signal word
Danger
Hazard statements
H302, H341, H350
Precautionary statements
P201, P281, P308+P313
Legal status
  • BR: Class D1 (Drug precursors)[2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

Safrole is an organic compound with the formula CH2O2C6H3CH2CH=CH2. It is a colorless oily liquid, although impure samples can appear yellow. A member of the phenylpropanoid family of natural products, it is found in sassafras plants, among others. Small amounts are found in a wide variety of plants, where it functions as a natural antifeedant.[3] Ocotea pretiosa,[4] which grows in Brazil, and Sassafras albidum,[3] which grows in eastern North America, are the main natural sources of safrole. It has a characteristic "sweet-shop" aroma.

It is a precursor in the synthesis of the insecticide synergist piperonyl butoxide, the fragrance piperonal via isosafrole, and the empathogenic/entactogenic substance MDMA.

  1. ^ Merck Index (11th ed.). 8287.
  2. ^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-15.
  3. ^ a b Kamdem, Donatien; Gage, Douglas (2007). "Chemical Composition of Essential Oil from the Root Bark of Sassafras albidum". Planta Medica. 61 (6): 574–5. doi:10.1055/s-2006-959379. PMID 8824955.
  4. ^ Hickey, Michael J. (1948). "Investigation of the chemical constituents of Brazilian sassafras oil". Journal of Organic Chemistry. 13 (3): 443–6. doi:10.1021/jo01161a020. PMID 18863852.

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Safrole

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Safrole is an organic compound with the formula CH2O2C6H3CH2CH=CH2. It is a colorless oily liquid, although impure samples can appear yellow. A member...

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Root beer

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common use is to add vanilla ice cream to make a root beer float. Since safrole, a key component of sassafras, was banned by the U.S. Food and Drug Administration...

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Sassafras albidum

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oil," which contains safrole, is generally a byproduct of camphor production in Asia or comes from related trees in Brazil. Safrole is a precursor for the...

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Sassafras

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Some small mammals also consume sassafras fruits. Sassafras oil contains safrole, which may have a carcinogenic effect. All parts of sassafras plants, including...

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Piperonyl butoxide

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pyrethrins, pyrethroids, and rotenone. It is a semisynthetic derivative of safrole and is produced from the condensation of the sodium salt of 2-(2-butoxyethoxy)...

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PiHKAL

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suggestions on legal plant sources of important drug precursors such as safrole. Through PIHKAL (and later TIHKAL), Shulgin sought to ensure that his discoveries...

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Boronia safrolifera

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Boronia safrolifera, commonly known as safrole boronia, is a species of flowering plant that is endemic to eastern Australia. It is an erect, woody shrub...

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MDMA

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turn is generally synthesized from piperonal, safrole or isosafrole. One method is to isomerize safrole to isosafrole in the presence of a strong base...

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Allylbenzene

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representation) of many phenylpropanoids. Prominent allylbenzenes include eugenol, safrole, and many others. "Allylbenzene". Hassam, Mohammad; Taher, Abu; Arnott...

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List of Australian herbs and spices

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chemovar, Cinnamon Myrtle Boronia safrolifera, safrole Crowea exalata, exalaticin Cinnamomum oliveri, safrole, Oliver's Cinnamon Cymbopogon refractus, Barbed...

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Magnoliids

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the oil's flavor is safrole, but it is no longer used in either the United States or Canada. Both nations banned the use of safrole as a food additive...

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Phenylpropanoid

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also derived from the monolignols. Examples include eugenol, chavicol, safrole, and estragole. These compounds are the primary constituents of various...

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Camphora officinarum

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called chemotypes, which are camphor, linalool, 1,8-cineole, nerolidol, safrole, and borneol. In China, field workers avoid mixing chemotypes when harvesting...

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Dandelion and burdock

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artificially rather than from the plant itself, in part because during the 1960s, safrole, the major component of the volatile oil of sassafras, was found to be...

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Piper auritum

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Piper auritum contains a relatively high concentration of hepatotoxic safrole, around 70%. A few of the other 40 constituents occurring in minor quantities...

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Tasmannia lanceolata

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has high antioxidant activity. Low safrole clonal selections are grown in plantations for commercial use, as safrole is considered a low-risk toxin. Used...

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Apiole

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1'-sulfoxy metabolite formation for apiole (3,4-OMe-safrole) is about 1/3 as active as safrole. No carcinogenicity was detected with parsley apiol or...

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Standard for the Uniform Scheduling of Medicines and Poisons

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or eyes. Examples: Arsenic Beryllium Bromethalin Chloroform Cyanamide Safrole Toluene Xylene Ziram Some of the above examples are subject to exceptions...

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Isosafrole

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essential oils, but is most commonly obtained by isomerizing the plant oil safrole. It exists as two geometric isomers, cis-isosafrole and trans-isosafrole...

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Food Additives Amendment of 1958

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example safrole, which occurs in sassafras and sweet basil. Even these substances are covered by the Delaney clause, so that, for example, safrole may not...

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Piperonal

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synthetic cherry flavoring. Due to their role in the manufacture of MDMA, safrole, isosafrole, and piperonal are Category I precursors under regulation no...

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Piper guineense

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contains significant proportions (up to around 10%) of myristicin, elemicin, safrole, and dillapiol, as well as some apiole (around 1.4%).[citation needed]...

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Betel

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of betel leaf varies geographically and is mostly chavibetol dominant. Safrole is a major component of Sri Lankan Piper betle. Eugenol, isoeugenol, and...

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Nutmeg oil

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various phenolic compounds and aromatic ethers, e.g. myristicin, elemicin, safrole, and methyl eugenol. The phenolic fraction is considered main contributor...

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Glossary of chemical formulae

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10601-19-1 C10H10N2O edaravone 89-25-8 C10H10N3NaO5 Suosan 140-46-5 C10H10O2 safrole C10H10O4 ferulic acid 1135-24-6 C10H11N3O3S sulfamethoxazole 723-46-6 C10H12N2...

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