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S9652

Sigma-Aldrich

Safrole

≥97%

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill):
C10H10O2
Numéro CAS:
Poids moléculaire :
162.19
Numéro Beilstein :
136380
Numéro CE :
Numéro MDL:
Code UNSPSC :
12352200
ID de substance PubChem :
Nomenclature NACRES :
NA.25

Pression de vapeur

1 mmHg ( 63.8 °C)

Niveau de qualité

Pureté

≥97%

Couleur

yellow

Indice de réfraction

n20/D 1.537 (lit.)

Point d'ébullition

232-234 °C (lit.)

Pf

11.2 °C (lit.)

Densité

1.095 g/mL at 25 °C (lit.)

Application(s)

metabolomics
vitamins, nutraceuticals, and natural products

Chaîne SMILES 

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

Clé InChI

ZMQAAUBTXCXRIC-UHFFFAOYSA-N

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Description générale

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).

Actions biochimiques/physiologiques

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.

Autres remarques

Principal constituent of sassafras oil

Pictogrammes

Health hazardExclamation mark

Mention d'avertissement

Danger

Mentions de danger

Classification des risques

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

Code de la classe de stockage

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

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

212.0 °F - closed cup

Point d'éclair (°C)

100 °C - closed cup

Équipement de protection individuelle

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter


Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

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)
Chapter 3-Families of compounds that occur in essential oils
Essential Chemistry for Aromatherapy, 41-77 (2008)
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)
Naoki Shinohara et al.
ChemMedChem, 7(10), 1770-1773 (2012-04-11)
Chemical point mutation: Polytheonamide B is a naturally occurring polypeptide containing 48 amino acids. It both displays potent cytotoxicity and acts as a monovalent cation channel in vitro. Chemoselective methods to modify the 44th, N-, and C-terminal residues of the
Erryana Martati et al.
Toxicological sciences : an official journal of the Society of Toxicology, 128(2), 301-316 (2012-05-17)
A physiologically based biokinetic (PBBK) model for the alkenylbenzene safrole in humans was developed based on in vitro- and in silico-derived kinetic parameters. With the model obtained, the time- and dose-dependent formation of the proximate and ultimate carcinogenic metabolites, 1-hydroxysafrole

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