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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:
94-59-7
Poids moléculaire :
162.19
Numéro Beilstein :
136380
Numéro CE :
202-345-4
Numéro MDL:
MFCD00005841
Code UNSPSC :
12352200
ID de substance PubChem :
24899851
Nomenclature NACRES :
NA.25

Pression de vapeur

1 mmHg ( 63.8 °C)

Niveau de qualité

200

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
GHS08,GHS07

Mention d'avertissement

Danger

Mentions de danger

H302,H315,H341,H350

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

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)
Le Su et al.
Toxicology letters, 217(2), 129-136 (2012-12-29)
Safrole-2',3'-oxide (SFO) is the major electrophilic metabolite of safrole (4-allyl-1, 2-methylenedioxybenzene), a natural plant constituent found in essential oils of numerous edible herbs and spices and in food containing these herbs, such as pesto sauce, cola beverages and bologna sausages.
Danielle S Fisher et al.
Therapeutic drug monitoring, 34(4), 415-421 (2012-07-11)
N-Desalkylquetiapine may be a pharmacologically active quetiapine metabolite. However, information on plasma concentrations of N-desalkylquetiapine and other quetiapine metabolites attained during quetiapine therapy is scant. The aim of this study was to investigate plasma concentrations of quetiapine, N-desalkylquetiapine, O-desalkylquetiapine, 7-hydroxyquetiapine
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