Skip to Content
Merck
All Photos(2)

Documents

S9652

Sigma-Aldrich

Safrole

≥97%

Synonym(s):

4-Allyl-1,2-methylenedioxybenzene, 5-Allyl-1,3-benzodioxole

Sign Into View Organizational & Contract Pricing


About This Item

Empirical Formula (Hill Notation):
C10H10O2
CAS Number:
Molecular Weight:
162.19
Beilstein:
136380
EC Number:
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.25

vapor pressure

1 mmHg ( 63.8 °C)

Quality Level

Assay

≥97%

color

yellow

refractive index

n20/D 1.537 (lit.)

bp

232-234 °C (lit.)

mp

11.2 °C (lit.)

density

1.095 g/mL at 25 °C (lit.)

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

SMILES string

C=CCc1ccc2OCOc2c1

InChI

1S/C10H10O2/c1-2-3-8-4-5-9-10(6-8)12-7-11-9/h2,4-6H,1,3,7H2

InChI key

ZMQAAUBTXCXRIC-UHFFFAOYSA-N

Looking for similar products? Visit Product Comparison Guide

General description

Safrole is used as a counter irritant and for treating parasitic infections.

Application

Safrole has been used to investigate the role of aldehyde dehydrogenase 3A1 (ALDH3A1) in conferring cisplatin resistance to head and neck squamous cell carcinoma (HNSCC).

Biochem/physiol Actions

Safrole is one of the vital food‐borne phytotoxins. It is present in various natural products such as spices including anise, basil, nutmeg and pepper. It exhibits cytotoxic effect in human tongue squamous carcinoma SCC‐4 cells by promoting apoptosis via mitochondria‐ and caspase‐dependent signal pathways.
Safrole is a naturally-occurring genotoxic compound found in Sassafras root and Areca (betel) quid. It is a hepatocarcinogen, and safrole-DNA adducts have also been seen in oral cancers of Areca users. Metabolites of safrole form adducts with DNA and induce chromasomal aberrations and sister chromatid exchanges.

Other Notes

Principal constituent of sassafras oil

Pictograms

Health hazardExclamation mark

Signal Word

Danger

Hazard Statements

Hazard Classifications

Acute Tox. 4 Oral - Carc. 1B - Muta. 2 - Skin Irrit. 2

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

212.0 °F - closed cup

Flash Point(C)

100 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Targeting aldehyde dehydrogenase activity in head and neck squamous cell carcinoma with a novel small molecule inhibitor
Kim J, et al.
Oncotarget, 8(32), 52345-52345 (2017)
Chapter 3-Families of compounds that occur in essential oils
Essential Chemistry for Aromatherapy, 41-77 (2008)
Safrole induces cell death in human tongue squamous cancer SCC-4 cells through mitochondria-dependent caspase activation cascade apoptotic signaling pathways
FS Yu, et al.
Environmental Toxicology, 27(7), 433-444 (2012)
M Jin et al.
Toxicology, 290(2-3), 312-321 (2011-10-26)
In order to investigate a medium-term animal model using reporter gene transgenic rodents in which general toxicity, genotoxicity and carcinogenicity are evaluated, F344 gpt delta rats were given a diet containing 0.1% and 0.5% (a carcinogenic dose) safrole for 13
M-J Fan et al.
Human & experimental toxicology, 31(9), 898-904 (2012-04-26)
Safrole, a component of piper betle inflorescence, is a documented rodent hepatocarcinogen and inhibits bactericidal activity and the release of superoxide anion (O(2-)) by polymorphonuclear leukocytes (PMNs). In the present study, we investigated the effects of safrole on immune responses

Articles

DNA damage and repair mechanism is vital for maintaining DNA integrity. Damage to cellular DNA is involved in mutagenesis, the development of cancer among others.

Cancer research has revealed that the classical model of carcinogenesis, a three step process consisting of initiation, promotion, and progression, is not complete.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service