This product is not food grade and intended for research use only. Currently, a food grade product option is not available.
M2028
Capsaicin
from Capsicum sp., ≥95% (HPLC), powder, TRPV1 agonist
Synonym(s):
8-Methyl-N-vanillyl-trans-6-nonenamide
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50 MG
$86.50
250 MG
$301.00
1 G
$911.00
About This Item
Linear Formula:
(CH3)2CHCH=CH(CH2)4CONHCH2C6H3-4-(OH)-3-(OCH3)
CAS Number:
Molecular Weight:
305.41
Beilstein/REAXYS Number:
2816484
EC Number:
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77
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Product Name
Capsaicin, ≥95%, from Capsicum sp.
biological source
Capsicum sp.
Quality Level
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[1] 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.[2] Capsaicin activates its receptor transient receptorpotential vanilloid subfamily member 1 (TRPV1) and activates sensory afferentneurons[3] 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.[4]
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.
signalword
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
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
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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)
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
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
Capsaicin upregulates HDAC2 via TRPV1 and impairs neuronal maturation in mice.
Wang S, et al.
Experimental & Molecular Medicine, 50(3), e455-e455 (2018)
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