Safrol

Safrole

Names
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 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:8994 N
ChemSpider	13848731 Y
ECHA InfoCard	100.002.133
KEGG	C10490 Y
InChI InChI=1S/C10H10O2/c1-2-3-8-4-5-9-10(6-8)12-7-11-9/h2,4-6H,1,3,7H2 Y Key: ZMQAAUBTXCXRIC-UHFFFAOYSA-N Y 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	162.19 g/mol
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
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

Safrole is a phenylpropene. It is a colorless or slightly yellow oily liquid typically extracted from the root-bark or the fruit of sassafras plants in the form of sassafras oil (although commercially available culinary sassafras oil is usually devoid of safrole due to a rule passed by the FDA in 1960), or is synthesized from catechol or 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. 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, are the main natural sources for 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 drug MDMA.

Safrole (4-allyl-1,2-methylenedioxybenzene or shikimol) is a phenylpropene. It is a colourless or slightly yellow oily liquid which is typically extracted from the root-bark or the fruit of Sassafras albidum (native to eastern north America) in the form of sassafras oil, or from Ocotea odorifera, a Brazilian species. It can also be synthesized from catechol or other related methylenedioxy compounds. Safrole is also present in certain essentials oils and in brown camphor oil, which is in small amounts present in many plants and functions as a natural pesticide. Safrole is a member of the methylenedioxybenzene group, of which many compounds are used as insecticide synergists; for example, safrole is used as a precursor in the synthesis of the insecticide piperonyl butoxide. Safrole is also used as a precursor in the synthesis of the drug N-methyl-3,4-methylenedioxyamphetamine (MDMA, Ecstasy). Safrole can be found in anise, nutmeg, cinnamon, and black pepper, and as an additive in root beer, chewing gum, toothpaste, soaps, and certain pharmaceutical preparations. Before safrole was banned by the FDA in 1960 for use in food, it was used as a food flavour for its characteristic ‘candy-shop’ aroma. Safrole has been shown to exhibit antibiotic and anti-angiogenic functions.