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Related CAS#:
404-86-4 25775-90-0
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404-86-4

404-86-4 structure
404-86-4 structure
  • Name: capsaicin
  • Chemical Name: capsaicin
  • CAS Number: 404-86-4
  • Molecular Formula: C18H27NO3
  • Molecular Weight: 305.412
  • Catalog: Biochemical Natural product
  • Create Date: 2018-02-07 08:00:00
  • Modify Date: 2024-01-02 12:43:09
  • Capsaicin is a TRPV1 agonist with an EC50 of 0.29 μM in HEK293 cells.
Name capsaicin
Synonyms (E)-Capsaicin
8-Methyl-N-vanillyl-trans-6-nonenamide
(E)-8-Methyl-N-vanillyl-6-nonenamide
(6E)-N-(4-Hydroxy-3-methoxybenzyl)-8-methyl-6-nonenamide
(E)-N-((4-Hydroxy-3-methoxyphenyl)methyl)-8-methyl-6-nonenamide
MFCD00017259
CAPSAICINE
Zostrix
trans-Capsaicin
Qutenza
(E)-N-[(4-hydroxy-3-methoxyphenyl)methyl]-8-methylnon-6-enamide
8-Methyl-N-vanillyl-6-nonenamide
6-Nonenamide, N-((4-hydroxy-3-methoxyphenyl)methyl)-8-methyl-, (E)-
capsaicin
(E)-N-(4-hydroxy-3-methoxybenzyl)-8-methylnon-6-enamide
6-Nonenimidic acid, N-[(4-hydroxy-3-methoxyphenyl)methyl]-8-methyl-, (1Z,6E)-
Transacin
Capsaicin (Natural)
trans-8-methyl-n-vanillyl-6-nonenamide
(6E)-N-(4-Hydroxy-3-methoxybenzyl)-8-methylnon-6-enamide
N-vanillyl-8-methyl-non-6-enamide
(1Z,6E)-N-(4-Hydroxy-3-methoxybenzyl)-8-methyl-6-nonenimidic acid
Styptysat
N-[(4-Hydroxy-3-methoxyphenyl)methyl]-8-methyl-6-nonenamide
Axsain
Capsidol
6-Nonenamide, N-[(4-hydroxy-3-methoxyphenyl)methyl]-8-methyl-, (6E)-
8-Methyl-N-vanillyl-trans-6-nonenamide,Capsaicin
8-Methyl-N-vanillyl-6-nonenamide, (E)-
8-methyl N-vanillyl-6-nonenamide
EINECS 206-969-8
Capsaicin, (6E)-
Description Capsaicin is a TRPV1 agonist with an EC50 of 0.29 μM in HEK293 cells.
Related Catalog
Target

EC50: 290 nM (hTRPV1, in HEK293 cell)[1]

In Vitro Capsaicin is an agonist of transient receptor potential vanilloid subtype 1 (TRPV1), which is expressed in nociceptive sensory neurons and a range of secretory epithelia, including salivary glands. Capsaicin activates TRPV1, which modulates the permeability of tight junctions (TJ) by regulating the expression and function of putative intercellular adhesion molecules in an ERK-dependent manner[2]. Capsaicin is found to inhibit the growth and proliferation of FaDu cells in a dose- and time-dependent manner. Cells treated with 50, 100, 200, and 300 µM Capsaicin show an augmented decrease in cell growth as the Capsaicin dose increases. In addition, the percentage of viable cells decreases as the incubation time increases. The observed IC50 value is around 150 µM[3].
In Vivo Capsaicin (CAP)-treated animals (Group IV) show increased DNA fragmentation suggesting apoptosis when compare with B(a)P-induced lung cancer-bearing animals (Group II) that show reduced DNA fragmentation. CAP-treated Group IV animals show markedly increased expressions of p53, Bax and caspase-3 with remarkable decrease in the levels of anti-apoptotic protein Bcl-2, when compare with B(a)P-administered lung cancer animals of Group II[4]. Capsaicin causes a dose-dependent reduction of tear secretion in female Wistar/ST rats. Significant effects are observed at doses of 20, 50 and 100 mg/kg. In addition, Capsaicin also causes corneal lesions, and significant effects are observed at doses of 50 and 100 mg/kg[5].
Cell Assay FaDu cells are plated at a density of 1×105 cells/well on 24-well plate. After overnight growth, the cells are treated with various concentrations of Capsaicin (0 μM, 50 μM, 100 μM, 150 μM, 200 μM, 250 μM, 300 μM, and 350 μM) for 24, 48 and 72 hours, with medium replacement every 24 hours. At the end of treatment, 30 µL of the tetrazolium compound MTT, and 270 µL of fresh medium are added. After further incubation for 4 hours at 37°C, 200 µL of 0.1 N HCl in 10% SDS is added into each well to dissolve the tetrazolium crystals. Finally, the absorbance at a wavelength of 540 nm is recorded using an ELISA plate reader[3].
Animal Admin Mice[4] Healthy male Swiss albino mice weighing 20-25 g (8-10 weeks old) are divided into four groups of six mice each as follows. Group I: control animals receive olive oil throughout the course of the experiment. Group II: animals are administered with Benzo(a)pyrene (B(a)P) (50 mg/kg body weight dissolved in olive oil) orally twice a week for four successive weeks. Group III: animals receive Capsaicin alone (10 mg/kg body weight dissolved in olive oil) intraperitoneally once in a week for 14 weeks to assess the cytotoxicity (if any) induced by Capsaicin. Group IV: animals receive B(a)P (as in Group II) along with Capsaicin (10 mg/kg b.wt dissolves in olive oil) intraperitoneally. Capsaicin treatment is started one week prior to the first dose of B(a)P administration and continued for 14 weeks. Rats[5] Female Wistar/ST rats, 4 d of age, are used. On postnatal day 4, rats are given a single subcutaneous injection of Capsaicin at a dose of 50 mg/kg (or 20 and 100 mg/kg for the dose-response test) dissolved in physiological saline containing 10% ethanol and 10% Tween 80. Vehicle-treated rats receive the vehicle solution alone. The injected rats are housed with their mothers, who are fed standard rat chow and maintained under normal conditions. At 4 weeks of age, the injected rats are separated and housed in cages, and maintained under normal conditions until the initiation of experiments.
References

[1]. McNamara FN, et al. Effects of piperine, the pungent component of black pepper, at the human vanilloid receptor (TRPV1). Br J Pharmacol. 2005 Mar;144(6):781-90.

[2]. Shin YH, et al. The Effect of Capsaicin on Salivary Gland Dysfunction. Molecules. 2016 Jun 25;21(7).

[3]. Le TD, et al. Capsaicin-induced apoptosis of FaDu human pharyngeal squamous carcinoma cells. Yonsei Med J. 2012 Jul 1;53(4):834-41.

[4]. Anandakumar P, et al. Capsaicin provokes apoptosis and restricts benzo(a)pyrene induced lung tumorigenesis in Swiss albino mice. Int Immunopharmacol. 2013 Jun 6;17(2):254-259.

[5]. Kagawa Y, et al. Investigation of capsaicin-induced superficial punctate keratopathy model due to reduced tear secretion in rats. Curr Eye Res. 2013 Jul;38(7):729-35.

[6]. Wang J, et al. Anti-inflammatory and retinal protective effects of capsaicin on ischaemia-induced injuries through the release of endogenous somatostatin. Clin Exp Pharmacol Physiol. 2017 Jul;44(7):803-814.
Density 1.0±0.1 g/cm3
Boiling Point 469.7±55.0 °C at 760 mmHg
Melting Point 62-65 °C(lit.)
Molecular Formula C18H27NO3
Molecular Weight 305.412
Flash Point 237.9±31.5 °C
Exact Mass 305.199097
PSA 58.56000
LogP 4.27
Vapour Pressure 0.0±1.2 mmHg at 25°C
Index of Refraction 1.508
Stability Stable. Incompatible with strong oxidizing agents.
Water Solubility insoluble

CHEMICAL IDENTIFICATION

RTECS NUMBER :
RA8530000
CHEMICAL NAME :
6-Nonenamide, N-((4-hydroxy-3-methoxyphenyl)methyl)-8-methyl-, (E)-
CAS REGISTRY NUMBER :
404-86-4
BEILSTEIN REFERENCE NO. :
2816484
LAST UPDATED :
199712
DATA ITEMS CITED :
23
MOLECULAR FORMULA :
C18-H27-N-O3
MOLECULAR WEIGHT :
305.46
WISWESSER LINE NOTATION :
1OR BQ E1MV5U1Y1&1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
9500 ug/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold Behavioral - excitement Behavioral - muscle contraction or spasticity
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
47200 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Administration onto the skin
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
>512 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
6500 ug/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold Behavioral - excitement Behavioral - muscle contraction or spasticity
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
9000 ug/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold Behavioral - excitement Behavioral - muscle contraction or spasticity
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
400 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intramuscular
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
7800 ug/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold Behavioral - excitement Behavioral - muscle contraction or spasticity
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intratracheal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
1600 ug/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold Behavioral - excitement Behavioral - muscle contraction or spasticity
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Rectal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
>218 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Mammal - cat
DOSE/DURATION :
1600 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
>50 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - guinea pig
DOSE/DURATION :
1100 ug/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold Behavioral - excitement Behavioral - muscle contraction or spasticity
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - hamster
DOSE/DURATION :
>120 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
2400 mg/kg/2W-I
TOXIC EFFECTS :
Behavioral - food intake (animal) Nutritional and Gross Metabolic - weight loss or decreased weight gain
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
3318 mg/kg/5W-C
TOXIC EFFECTS :
Tumorigenic - equivocal tumorigenic agent by RTECS criteria Gastrointestinal - tumors
TYPE OF TEST :
Micronucleus test
TYPE OF TEST :
DNA inhibition
TYPE OF TEST :
Sister chromatid exchange

MUTATION DATA

TYPE OF TEST :
Mutation in microorganisms
TEST SYSTEM :
Rodent - hamster Lung
DOSE/DURATION :
5 mg/L
REFERENCE :
CALEDQ Cancer Letters (Shannon, Ireland). (Elsevier Scientific Pub. Ireland Ltd., POB 85, Limerick, Ireland) V.1- 1975- Volume(issue)/page/year: 48,109,1989 *** U.S. STANDARDS AND REGULATIONS *** EPA FIFRA 1988 PESTICIDE SUBJECT TO REGISTRATION OR RE-REGISTRATION FEREAC Federal Register. (U.S. Government Printing Office, Supt. of Documents, Washington, DC 20402) V.1- 1936- Volume(issue)/page/year: 54,7740,1989
Symbol GHS06 GHS08
GHS06, GHS08
Signal Word Danger
Hazard Statements H301-H315-H317-H319-H334-H335
Precautionary Statements P261-P280-P301 + P310-P305 + P351 + P338-P342 + P311
Personal Protective Equipment Eyeshields;Faceshields;Gloves;type P2 (EN 143) respirator cartridges
Hazard Codes T:Toxic
Risk Phrases R25;R37/38;R41;R42/43
Safety Phrases S22-S26-S28-S36/39-S45
RIDADR UN 2811 6.1/PG 2
WGK Germany 3
RTECS RA8530000
Packaging Group II
Hazard Class 6.1(a)
HS Code 2932999099
HS Code 2924299090
Summary 2924299090. other cyclic amides (including cyclic carbamates) and their derivatives; salts thereof. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%

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