360376

Capsaicin

63.7% (HPLC), powder, TRPV1 agonist

• Synonym(s): 8-Methyl-N-vanillyl-trans-6-nonenamide
• Linear Formula: (CH₃)₂CHCH=CH(CH₂)₄CONHCH₂C₆H₃-4-(OH)-3-(OCH₃)
• CAS Number: 404-86-4
• Molecular Weight: 305.41
• Beilstein/REAXYS Number: 2816484
• EC Number: 206-969-8
• MDL number: MFCD00017259
• UNSPSC Code: 12352200
• PubChem Substance ID: 57649462
• NACRES: NA.77

Properties

• product name: Capsaicin, natural
• grade: natural
• assay: 63.7% (HPLC)
• form: powder
• composition: capsaicin, 65% ; dihydrocapsaicin, 35%
• mp: 62-65 °C (lit.)
• solubility: chloroform: 5%
• storage temp.: 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+
• InChI key: YKPUWZUDDOIDPM-SOFGYWHQSA-N
• Gene Information: human ... CYP1A2(1544) , TRPV1(7442) ; rat ... Trpv1(83810) , Trpv4(66026)

Description

General description

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.

Application

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 Actions

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).

Prototype vanilloid receptor agonist. Neurotoxin; activates sensory neurons that give rise to unmyelinated C-fibers, many of which contain substance P. Topical application desensitizes the sensory nerve endings giving a paradoxical antinociceptive effect; systemic administration can be neurotoxic to capsaicin-sensitive cells, especially in newborn animals. Active component of chili peppers.

Safety Information

• pictograms: GHS06,GHS08,GHS05
• signalword: Danger
• hcodes: H300,H315,H317,H318,H334,H335
• pcodes: P261 - P264 - P280 - P301 + P310 - P302 + P352 - P305 + P351 + P338
• Hazard Classifications: Acute Tox. 2 Oral - Eye Dam. 1 - Resp. Sens. 1 - Skin Irrit. 2 - Skin Sens. 1 - STOT SE 3
• target_organs: Respiratory system
• Storage Class: 6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials
• wgk_germany: WGK 3
• flash_point_f: 235.4 °F - closed cup
• flash_point_c: 113 °C - closed cup
• ppe: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges