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M2028

Sigma-Aldrich

Capsaicin

≥95%, from Capsicum sp.

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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:
2816484
EC Number:
206-969-8
MDL number:
MFCD00017259
UNSPSC Code:
12352200
PubChem Substance ID:
24896598
NACRES:
NA.77

biological source

Capsicum sp.

Quality Level

200

Assay

≥95%

mp

62-65 °C (lit.)

solubility

H2O: insoluble
ethanol: soluble

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)

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General description

Capsaicin is an alkaloid that is present inthe fruit of the Capsicum genus and is the main reason for the spicy flavor inhot peppers including jalapenos, habaneros, and red chili peppers. It isobserved that capsaicin acts as a chemoprotective agent and can induceapoptosis, inhibit proliferation, and induce cell-cycle arrest in variouscancer cells. Capsaicin activates its receptor transient receptorpotential vanilloid subfamily member 1 (TRPV1) and activates sensory afferentneurons that causes neurogenicinflammation, hypothermia, and pain.

Application

Capsaicin has also been used asa TRPV1 agonist to study the effect of barbamide on capsaicin response indorsal root ganglion sensory neurons.
Capsaicin has been used:
  • to study its effects on chromatin remodeling and gene expression related to synaptic plasticity
  • to study TRPV1 channel signaling in H2C1 cells (which are human embryonic kidney 293 cells expressing TRPV1 channels)

Biochem/physiol Actions

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.

Signal Word

Danger

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

WGK

WGK 3

Flash Point(F)

235.4 °F

Flash Point(C)

113 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

监管及禁止进口产品

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Capsaicin upregulates HDAC2 via TRPV1 and impairs neuronal maturation in mice.
Wang S, et al.
Experimental & Molecular Medicine, 50(3), e455-e455 (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
Stimulation of TRPV1 channels activates the AP-1 transcription factor.
Backes TM, et al.
Biochemical Pharmacology, 150(3), 160-169 (2018)
Chemical and Pharmacological Aspects of Capsaicin
Maria D, et al.
Molecules (Basel), 16(2), 1253-1270 (2011)
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