M2028
Capsaicin
from Capsicum sp., ≥95% (HPLC), powder, TRPV1 agonist
동의어(들):
8-Methyl-N-vanillyl-trans-6-nonenamide
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크기 선택
제품정보 (DICE 배송 시 비용 별도)
Linear Formula:
(CH3)2CHCH=CH(CH2)4CONHCH2C6H3-4-(OH)-3-(OCH3)
CAS 번호:
Molecular Weight:
305.41
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12352200
EC Number:
206-969-8
MDL number:
Beilstein/REAXYS Number:
2816484
Assay:
≥95%
Quality level:
제품 이름
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 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 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)
Capsaicin has also been used asa TRPV1 agonist to study the effect of barbamide on capsaicin response indorsal root ganglion sensory neurons.
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.
Prototype vanilloid receptor agonist; neurotoxin. 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
저장 등급
6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials
wgk
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
Stimulation of TRPV1 channels activates the AP-1 transcription factor.
Backes TM, et al.
Biochemical Pharmacology, 150(3), 160-169 (2018)
Capsaicin upregulates HDAC2 via TRPV1 and impairs neuronal maturation in mice.
Wang S, et al.
Experimental & Molecular Medicine, 50(3), e455-e455 (2018)
Amol M Patwardhan et al.
Proceedings of the National Academy of Sciences of the United States of America, 106(44), 18820-18824 (2009-10-22)
Transient receptor potential vanilloid 1 (TRPV1) plays a major role in hyperalgesia and allodynia and is expressed both in the peripheral and central nervous systems (CNS). However, few studies have evaluated mechanisms by which CNS TRPV1 mediates hyperalgesia and allodynia
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
Seon-Hee Oh et al.
The Journal of pharmacology and experimental therapeutics, 329(1), 112-122 (2009-01-14)
Endoplasmic reticulum (ER) stress causes cell survival or death, which is dependent on the type of cell and stimulus. Capsaicin (8-methyl-N-vanillyl-6-nonenamide) and its analog, dihydrocapsaicin (DHC), induced caspase-3-independent/-dependent signaling pathways in WI38 lung epithelial fibroblast cells. Here, we describe the
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