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Name	Capsaicin	EINECS	206-969-8
CAS No.	404-86-4	Density	1.041 g/cm³
PSA	58.56000	LogP	4.18050
Solubility	insoluble in water	Melting Point	62-65 °C(lit.)
Formula	C₁₈H₂₇NO₃	Boiling Point	511.5 °C at 760 mmHg
Molecular Weight	305.417	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		Hazard Symbols	T, T+
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;	Article Data	18

Capsaicin Synthetic route

: 1196-92-5
Vanillylamin

: 95636-02-5
(E)-8-Methylnon-6-enoic acid chloride

: 404-86-4
capsaicin

Conditions

Conditions	Yield
Stage #1: Vanillylamin With sodium hydrogencarbonate In chloroform; water at 20℃; for 0.75h; Stage #2: (E)-8-Methylnon-6-enoic acid chloride In chloroform; water at 20 - 40℃; for 1h;	91%
In diethyl ether for 72h; Ambient temperature;
In diethyl ether 1.) RT, 2 h, 2.) reflux, 2 h; Yield given;

: 59320-77-3
trans-8-methyl-6-nonenoic acid

: 7149-10-2
vanillylamine hydrochloride

: 404-86-4
capsaicin

Conditions

Conditions	Yield
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine In N,N-dimethyl-formamide at 20℃; for 2h; Schlenk technique;	75%

: 59320-77-3
trans-8-methyl-6-nonenoic acid

: 404-86-4
capsaicin

Conditions

Conditions	Yield
With thionyl chloride Behandeln des Reaktionsprodukts mit 4-Aminomethyl-2-methoxy-phenol in Aether;
Multi-step reaction with 2 steps 1: SOCl2 / 2 h / Heating 2: diethyl ether / 2 h / Heating View Scheme
Multi-step reaction with 2 steps 1: SOCl2 / 2 h / Heating 2: diethyl ether View Scheme

: (E)-N-[(4β-D-glucopyranosyloxy)-3-methoxyphenylmethyl]-8-methylnon-6-enamide

A: 2280-44-6
D-Glucose

B: 404-86-4
capsaicin

Conditions

Conditions	Yield
at 37℃; for 16h; β-glucosidase; enzymatic hydrolysis of capsaicin glucoside with α- or β-glucosidase;

: 59721-82-3
(E)-1-hydroxy-6-methylhept-4-ene

: 404-86-4
capsaicin

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: Et3N / CH2Cl2 / 1.) 0 deg C, 30 min, 2.) RT, 1 h 2: 1.) NaH, 2.) KI / 1.) DMF, THF, RT, 15 min, 2.) DMF, THF, 80 deg C, 3.5 h 3: 86 percent / DMSO, NaCl / H2O / 3 h / 170 °C 4: 92 percent / aq. NaOH / methanol / 15 h / Heating 5: SOCl2 / 2 h / Heating 6: diethyl ether / 2 h / Heating View Scheme
Multi-step reaction with 3 steps 1: pyridine; phosphorus (III)-bromide 2: ethanol / und Erwaermen des Reaktionsprodukts mit wss.Kalilauge und Erhitzen des nach dem Ansaeuern isolierten Reaktionsprodukts bis auf 180grad 3: SOCl2 / Behandeln des Reaktionsprodukts mit 4-Aminomethyl-2-methoxy-phenol in Aether View Scheme

: 179617-41-5
Methanesulfonic acid (E)-6-methyl-hept-4-enyl ester

: 404-86-4
capsaicin

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 1.) NaH, 2.) KI / 1.) DMF, THF, RT, 15 min, 2.) DMF, THF, 80 deg C, 3.5 h 2: 86 percent / DMSO, NaCl / H2O / 3 h / 170 °C 3: 92 percent / aq. NaOH / methanol / 15 h / Heating 4: SOCl2 / 2 h / Heating 5: diethyl ether / 2 h / Heating View Scheme

: 112375-54-9
(E)-methyl 8-methyl-6-nonenoate

: 404-86-4
capsaicin

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 92 percent / aq. NaOH / methanol / 15 h / Heating 2: SOCl2 / 2 h / Heating 3: diethyl ether / 2 h / Heating View Scheme
Multi-step reaction with 3 steps 1: aq. KOH / ethanol / 1 h / Heating 2: thionyl chloride / 1.) RT, 18 h, 2.) 100 deg C, 30 min 3: diethyl ether / 72 h / Ambient temperature View Scheme

: 179617-47-1
trans-6-methyl-hept-4-enoic acid ethyl ester

: 404-86-4
capsaicin

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: 86 percent / LiAlH4 / diethyl ether / 15 h / Ambient temperature 2: Et3N / CH2Cl2 / 1.) 0 deg C, 30 min, 2.) RT, 1 h 3: 1.) NaH, 2.) KI / 1.) DMF, THF, RT, 15 min, 2.) DMF, THF, 80 deg C, 3.5 h 4: 86 percent / DMSO, NaCl / H2O / 3 h / 170 °C 5: 92 percent / aq. NaOH / methanol / 15 h / Heating 6: SOCl2 / 2 h / Heating 7: diethyl ether / 2 h / Heating View Scheme

Yield

Multi-step reaction with 7 steps
1: 86 percent / LiAlH4 / diethyl ether / 15 h / Ambient temperature
2: Et3N / CH2Cl2 / 1.) 0 deg C, 30 min, 2.) RT, 1 h
3: 1.) NaH, 2.) KI / 1.) DMF, THF, RT, 15 min, 2.) DMF, THF, 80 deg C, 3.5 h
4: 86 percent / DMSO, NaCl / H2O / 3 h / 170 °C
5: 92 percent / aq. NaOH / methanol / 15 h / Heating
6: SOCl2 / 2 h / Heating
7: diethyl ether / 2 h / Heating
View Scheme

: 179617-42-6
2-((E)-6-Methyl-hept-4-enyl)-malonic acid dimethyl ester

: 404-86-4
capsaicin

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 86 percent / DMSO, NaCl / H2O / 3 h / 170 °C 2: 92 percent / aq. NaOH / methanol / 15 h / Heating 3: SOCl2 / 2 h / Heating 4: diethyl ether / 2 h / Heating View Scheme

: 93545-84-7
6-hydroxyhexanal lactol

: 404-86-4
capsaicin

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: KOtBu / dimethylformamide / Ambient temperature 2: HNO3, NaNO2 / 1 h / 75 °C 3: 78 percent / CrO3 / acetone 4: SOCl2 / 2 h / Heating 5: diethyl ether View Scheme

Capsaicin Chemical Properties

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

Capsaicin 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.

Capsaicin Uses

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

Capsaicin 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.

Capsaicin Safety Profile

Hazard Codes of Capsaicin (CAS NO.404-86-4): Toxic T, Very T+
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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