360376

Capsaicin

63.7% (HPLC), powder, TRPV1 agonist

• Synonym(e): trans-8-Methyl-N-vanillyl-6-nonensäureamid
• Lineare Formel: (CH₃)₂CHCH=CH(CH₂)₄CONHCH₂C₆H₃-4-(OH)-3-(OCH₃)
• CAS-Nummer: 404-86-4
• Molekulargewicht: 305.41
• Beilstein: 2816484
• EG-Nummer: 206-969-8
• MDL-Nummer: MFCD00017259
• UNSPSC-Code: 12352200
• PubChem Substanz-ID: 57649462
• NACRES: NA.77

Eigenschaften

• product name: Capsaicin, natural
• Qualität: natural
• Assay: 63.7% (HPLC)
• Form: powder
• Zusammensetzung: capsaicin, 65% ; dihydrocapsaicin, 35%
• mp (Schmelzpunkt): 62-65 °C (lit.)
• Löslichkeit: chloroform: 5%
• Lagertemp.: 2-8°C
• SMILES String: COc1cc(CNC(=O)CCCC\C=C\C(C)C)ccc1O
• InChI: 1S/C18H27NO3/c1-14(2)8-6-4-5-7-9-18(21)19-13-15-10-11-16(20)17(12-15)22-3/h6,8,10-12,14,20H,4-5,7,9,13H2,1-3H3,(H,19,21)/b8-6+
• InChIKey: YKPUWZUDDOIDPM-SOFGYWHQSA-N
• Angaben zum Gen: human ... CYP1A2(1544) , TRPV1(7442) ; rat ... Trpv1(83810) , Trpv4(66026)

Beschreibung

Allgemeine Beschreibung

Capsaicin (Zostrix), an alkaloid extract is obtained from hot chili peppers. It is accessible in the form of cream and lotion. Capsaicin is a hydrophobic, instable and pungent white crystalline powder, that has no smell and color. It is produced by mixing a branched-chain fatty acid to vanillylamine in the chili pepper.

Anwendung

Capsaicin has been used in the development of the isolation methods. It has also been used in the development of enzyme based electrochemical biosensor for the determination of capsaicin using a novel signal amplification strategy.

Biochem./physiol. Wirkung

Prototyp Vanilloid-Rezeptoragonist; Neurotoxin; aktiviert sensorische Neuronen, was zu unmyelierten C-Fasern führt, von denen viele Substanz P enthalten. Topische Applikation desensibilisiert die sensorischen Nervenendigungen, was eine paradoxe antinozizeptive Wirkung ergibt; systemische Verabreichung kann neurotoxisch auf Capsaicin-sensitive Zellen wirken, insbesondere bei neugeborenen Tieren. Aktiver Bestandteil von Chilischoten.

Capsaicin is used as an important component of oleoresin capsicum or pepper spray. It plays a beneficial role in obesity, cardiovascular and gastrointestinal conditions, several cancers, neurogenic bladder and dermatologic conditions. It is used in the production of spices, chilli sauces and pain-inducing defensive pepper sprays. Capsaicin is also used to manufacture creams to treat diabetic neuropathy, cluster headache, psoriasis, rheumatoid arthritis and reflex sympathetic dystrophy. It is considered as an agonist of the transient receptor potential cation channel subfamily V member 1 (TrpV1).

Sicherheitshinweise

• Piktogramme: GHS06,GHS08,GHS05
• Signalwort: Danger
• H-Sätze: H300,H315,H317,H318,H334,H335
• P-Sätze: P261 - P264 - P280 - P301 + P310 - P302 + P352 - P305 + P351 + P338
• Gefahreneinstufungen: Acute Tox. 2 Oral - Eye Dam. 1 - Resp. Sens. 1 - Skin Irrit. 2 - Skin Sens. 1 - STOT SE 3
• Zielorgane: Respiratory system
• Lagerklassenschlüssel: 6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials
• WGK: WGK 3
• Flammpunkt (°F): 235.4 °F - closed cup
• Flammpunkt (°C): 113 °C - closed cup
• Persönliche Schutzausrüstung: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges