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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
Beilstein:
136380
Numéro CE :
202-345-4
Numéro MDL:
MFCD00005841
Code UNSPSC :
12352200
ID de substance PubChem :
24899851
Nomenclature NACRES :
NA.25
Le tarif et la disponibilité ne sont pas disponibles actuellement.

Pression de vapeur

1 mmHg ( 63.8 °C)

Niveau de qualité

200

Essai

≥97%

Couleur

yellow

Indice de réfraction

n20/D 1.537 (lit.)

pb

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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Catégories apparentées

Description générale

Safrole is used as a counter irritant and for treating parasitic infections.[1]

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).[2]

Actions biochimiques/physiologiques

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.
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.[3]

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

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Certificats d'analyse (COA)

Lot/Batch Number
0000331885
0000331884
0000331885
0000331884
BCCH4334

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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)
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)
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
Afficher tous les articles scientifiques apparentés

Articles

DNA Damage and Repair

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.

Carcinogenesis and Epigenetics

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

Questions

1–2 of 2 Questions  

  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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