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Merck
CN

M2028

Sigma-Aldrich

辣椒素

from Capsicum sp., ≥95% (HPLC), powder, TRPV1 agonist

别名:

8-甲基-N-香草基-反-6-壬烯胺

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关于此项目

线性分子式:
(CH3)2CHCH=CH(CH2)4CONHCH2C6H3-4-(OH)-3-(OCH3)
化学文摘社编号:
404-86-4
分子量:
305.41
Beilstein:
2816484
EC 号:
206-969-8
MDL编号:
MFCD00017259
UNSPSC代码:
12352200
PubChem化学物质编号:
24896598
NACRES:
NA.77

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产品名称

辣椒素, ≥95%, from Capsicum sp.

生物来源

Capsicum sp.

质量水平

200

方案

≥95%

mp

62-65 °C (lit.)

溶解性

H2O: insoluble
ethanol: soluble

储存温度

2-8°C

SMILES字符串

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

基因信息

human ... CYP1A2(1544), TRPV1(7442)
rat ... Trpv1(83810), Trpv4(66026)

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相关类别

一般描述

辣椒素是一种生物碱，存在于辣椒属植物的果实中，是墨西哥胡椒、哈瓦那辣椒、红辣椒等辣椒中辣味的主要来源。研究发现，辣椒素可作为化学保护剂，在各种癌细胞中诱导细胞凋亡、抑制增殖和诱导细胞周期停滞。辣椒素可激活瞬时受体电位香草酸受体1(TRPV1)，也能激活感觉传入神经元，引起神经性炎症、低温和疼痛。

应用

辣椒素也用作TRPV1激动剂，以研究barbamide（巴布酰胺）对背根神经节感觉神经元中辣椒素反应的影响。
辣椒素已被用于：
  • 研究其对与突触可塑性相关的染色质重塑和基因表达的影响
  • 研究H2C1细胞（表达TRPV1通道的人胚肾293细胞）中的TRPV1通道信号

生化/生理作用

原型香草受体激动剂。 神经毒素；激活产生无髓C纤维的感觉神经元，其中许多含有P物质。 局部使用可使感觉神经末梢脱敏，从而产生反常的抗伤害感受作用；全身给药可对辣椒素敏感的细胞产生神经毒性，尤其是在新生动物中。辣椒的活性成分。
原型香草受体激动剂；神经毒素。辣椒的活性成分。

警示用语：

Danger

危险分类

Acute Tox. 2 Oral - Eye Dam. 1 - Resp. Sens. 1 - Skin Irrit. 2 - Skin Sens. 1 - STOT SE 3

靶器官

Respiratory system

储存分类代码

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

闪点(°F)

235.4 °F - closed cup

闪点(°C)

113 °C - closed cup

个人防护装备

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

法规信息

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历史批次信息供参考:

分析证书(COA)

Lot/Batch Number
WXBF6110V
WXBF5353V
WXBF4163V
WXBF2612V
WXBF1534V

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  1. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

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    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

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Chemical and Pharmacological Aspects of Capsaicin
Maria D, et al.
Molecules (Basel), 16(2), 1253-1270 (2011)
Stimulation of TRPV1 channels activates the AP-1 transcription factor.
Backes TM, et al.
Biochemical Pharmacology, 150(3), 160-169 (2018)
Surinder Kumar Sharma et al.
European journal of pharmacology, 720(1-3), 55-62 (2013-11-12)
Capsaicin is the active ingredient of chili peppers and gives them the characteristic pungent flavor. Understanding the actions of capsaicin led to the discovery of its receptor, transient receptor potential vanilloid subfamily member 1 (TRPV1). This receptor is found on
Ann M Bode et al.
Cancer research, 71(8), 2809-2814 (2011-04-14)
Capsaicin (trans-8-methyl-N-vanillyl-6-nonenamide) is the principal pungent component in hot peppers, including red chili peppers, jalapeños, and habaneros. Consumed worldwide, capsaicin has a long and convoluted history of controversy about whether its consumption or topical application is entirely safe. Conflicting epidemiologic
Shao-Gang Lu et al.
Pain, 151(3), 633-643 (2010-10-05)
The impact of persistent inflammation on voltage-activated Ca(2+) channels in cutaneous DRG neurons from adult rats was assessed with whole cell patch clamp techniques, sqRT-PCR and Western blot analysis. Inflammation was induced with a subcutaneous injection of complete Freund's adjuvant
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