Safrole

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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.133 Edit this at Wikidata
EC Number
  • 202-345-4
KEGG
RTECS number
  • CY2800000
UNII
UN number 3082
  • 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
  • C=CCc1ccc2OCOc2c1
Properties
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)
−97.5×10−6 cm3/mol
Hazards
GHS labelling:
GHS07: Exclamation markGHS08: Health hazard
Danger
H302, H341, H350
P201, P281, P308+P313
Legal status
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 ?)

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.