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Capsaicin

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Name Capsaicin EINECS 206-969-8
CAS No. 404-86-4 Density 1.041 g/cm3
Solubility insoluble in water Melting Point 62-65 °C(lit.)
Formula C18H27NO3 Boiling Point 511.5 °C at 760 mmHg
Molecular Weight 305.42 Flash Point 263.1 °C
Transport Information UN 2811 6.1/PG 2 Appearance Off-white crystalline solid
Safety 22-26-28-36/39-45-36/37/39 Risk Codes 25-37/38-41-42/43-36/37/38
Molecular Structure Molecular Structure of 404-86-4 (Capsaicin) Hazard Symbols ToxicT, VeryT+
Synonyms

Styptysat;6-Nonenamide, 8-methyl-N-vanillyl-, (E)- (8CI);8-Methyl-N-vanillyl-6-nonenamide, (E)-;6-Nonenamide, N-[ (4-hydroxy-3-methoxyphenyl)methyl]-8-methyl-, (E)-;trans-8-Methyl-N-vanillyl-6-nonenamide;6-Nonenamide,N-[(4-hydroxy-3-methoxyphenyl) methyl]-8-methyl-,(6E)-;Capsaicin (JAN/USP);N-[(4-hydroxy-3-methoxy-phenyl)methyl]-8-methyl-non-6-enamide;(E)-N-[(4-hydroxy-3-methoxy-phenyl)methyl]-8-methyl-non-6-enamide;(E)-N-((4-Hydroxy-3-methoxyphenyl)-methyl)-8-methyl-6-nonenamide;Zostrix;Capsaicin [USAN];6-Nonenamide, 8-methyl-N-vanillyl-, (E)-;6-Nonenamide, N-((4-hydroxy-3-methoxyphenyl)methyl)-8-methyl-, (6E)-;Prestwick_204;Capsaicin [in oleoresin of capsicum];EPA Pesticide Chemical Code 070701;6-Nonenamide, N-((4-hydroxy-3-methoxyphenyl)methyl)-8-methyl-, (E)-;FEMA No. 3404;Zostrix (TN);Ratden PE 40;N-((4-Hydroxy-3-methoxyphenyl)methyl)-8-methyl-6-nonenamide, (E)-;N-(4-Hydroxy-3-methoxybenzyl)-8-methylnon-trans-6-enamide;(E)-8-Methyl-N-vanillyl-6-nonenamide;

 

Chemistry

Molecular Structure:

Molecular Formula: C18H27NO3
Molecular Weight: 305.4119
IUPAC Name: (E)-N-[(4-Hydroxy-3-methoxyphenyl)methyl]-8-methylnon-6-enamide
Synonyms of Capsaicin (CAS NO.404-86-4): (E)-8-Methyl-N-vanillyl-6-nonenamide ; (E)-N-((4-Hydroxy-3-methoxyphenyl)-methyl)-8-methyl-6-nonenamide ; 4-13-00-02588 (Beilstein Handbook Reference) ; 6-Nonenamide, (E)-N-((4-hydroxy-3-methoxy-phenyl)methyl)-8-methyl ; 6-Nonenamide, 8-methyl-N-vanillyl-, (E)- ; 6-Nonenamide, N-((4-hydroxy-3-methoxyphenyl)methyl)-8-methyl-, (E)- ; 8-Methyl-N-vanillyl-6-nonenamide, (E)- ; BRN 2816484 ; CCRIS 1588 ; Capsaicine ; Caswell No. 158 ; EINECS 206-969-8 ; EPA Pesticide Chemical Code 070701 ; FEMA No. 3404 ; HSDB 954 ; Isodecenoic acid vanillylamide ; N-((4-Hydroxy-3-methoxyphenyl)methyl)-8-methyl-6-nonenamide, (E)- ; N-(4-Hydroxy-3-methoxybenzyl)-8-methylnon-trans-6-enamide ; NCI-C56564 ; NSC 56353 ; Qutenza ; Styptysat ; UNII-S07O44R1ZM ; trans-8-Methyl-N-vanillyl-6-nonenamide
CAS NO: 404-86-4
Classification Code: Analgesic [topical] ; Antineuralgic, specific pain syndromes, topical ; Antipruritics ; Dermatologic Agents ; Mutation data ; Natural Product ; Peripheral Nervous System Agents ; Sensory System Agents ; Tumor data
Melting point: 62-65 °C 
Index of Refraction: 1.523
Molar Refractivity: 89.69 cm3
Molar Volume: 293.1 cm3
Surface Tension: 38.7 dyne/cm
Density: 1.041 g/cm3
Flash Point: 263.1 °C
Enthalpy of Vaporization: 81.2 kJ/mol
Boiling Point: 511.5 °C at 760 mmHg
Vapour Pressure: 4.41E-11 mmHg at 25°C

History

The molecule of capsaicin was first isolated in crystalline form in 1816 by P. A. Bucholz and again 30 years later by L.T. Thresh, who gave it the name "capsaicin". In 1878, the Hungarian doctor Endre Hogyes  isolated it and proved that it not only caused the burning feeling when in contact with mucous membranes but also increased secretion of gastric juice. Capsaicin was first synthesized in 1930 by E. Spath and S. F. Darling.

Uses

 Capsaicin (CAS NO.404-86-4) is used as a tool in neurobiological research. Prototype vanilloid receptor agonist. Topical analgesic.

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LDLo intravenous 1600ug/kg (1.6mg/kg)   FAO Nutrition Meetings Report Series. Vol. 48A, Pg. 60, 1970.
guinea pig LD50 intraperitoneal 1100ug/kg (1.1mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)

BEHAVIORAL: EXCITEMENT
Toxicon. Vol. 18, Pg. 215, 1980.
hamster LD50 intraperitoneal > 120mg/kg (120mg/kg)   Toxicon. Vol. 18, Pg. 215, 1980.
mouse LD50 intramuscular 7800ug/kg (7.8mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: EXCITEMENT

BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)
Toxicon. Vol. 18, Pg. 215, 1980.
mouse LD50 intraperitoneal 6500ug/kg (6.5mg/kg) BEHAVIORAL: EXCITEMENT

BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Toxicon. Vol. 18, Pg. 215, 1980.
mouse LD50 intratracheal 1600ug/kg (1.6mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: EXCITEMENT

BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)
Toxicon. Vol. 18, Pg. 215, 1980.
mouse LD50 intravenous 400ug/kg (0.4mg/kg)   Yakhak Hoe Chi. Journal of the Pharmaceutical Society. Vol. 25(3), Pg. 101, 1981.
mouse LD50 oral 47200ug/kg (47.2mg/kg)   Yakhak Hoe Chi. Journal of the Pharmaceutical Society. Vol. 25(3), Pg. 101, 1981.
mouse LD50 rectal > 218mg/kg (218mg/kg)   Toxicon. Vol. 18, Pg. 215, 1980.
mouse LD50 skin > 512mg/kg (512mg/kg)   Toxicon. Vol. 18, Pg. 215, 1980.
mouse LD50 subcutaneous 9000ug/kg (9mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)

BEHAVIORAL: EXCITEMENT
Toxicon. Vol. 18, Pg. 215, 1980.
rabbit LD50 intraperitoneal > 50mg/kg (50mg/kg)   Toxicon. Vol. 18, Pg. 215, 1980.
rat LD50 intraperitoneal 9500ug/kg (9.5mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: EXCITEMENT

BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)
Toxicon. Vol. 18, Pg. 215, 1980.

Safety Profile

Hazard Codes of Capsaicin (CAS NO.404-86-4): ToxicT,VeryT+
Risk Statements: 25-41-42/43-36/37/38 
R25: Toxic if swallowed. 
R41: Risk of serious damage to the eyes. 
R42/43: May cause sensitization by inhalation and skin contact. 
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements: 22-26-28-45-36/37/39 
S22: Do not breathe dust. 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S28: After contact with skin, wash immediately with plenty of soap-suds. 
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) 
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection.
RIDADR: UN 2811 6.1/PG 2
WGK Germany: 3
RTECS: RA8530000
F: 10-21
HazardClass: 6.1(a)
PackingGroup: II

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