Capsaicin supplier | CasNO.404-86-4

Name
Capsaicin
EINECS 206-969-8
CAS No. 404-86-4
Article Data18
CAS DataBase
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 305.417
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;
PSA 58.56000
LogP 4.18050

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

: 90369-18-9
(Z)-1-hydroxy-8-methylnon-6-ene

: 404-86-4
capsaicin

Conditions

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

: 90369-20-3
(E)-1-hydroxy-8-methylnon-6-ene

: 404-86-4
capsaicin

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 78 percent / CrO3 / acetone 2: SOCl2 / 2 h / Heating 3: diethyl ether View Scheme

: 50889-29-7
(5-carboxypentyl)triphenylphosphonium bromide

: 404-86-4
capsaicin

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: t-BuOK / dimethylformamide / 15 h / Ambient temperature 2: thionyl chloride / 1.) room temp., 8 h, 2.) 100 deg C, 0.5 h 3: diethyl ether / 1.) RT, 2 h, 2.) reflux, 2 h View Scheme
Multi-step reaction with 4 steps 1: t-BuOK / dimethylformamide / 15 h / Ambient temperature 2: 2M NaNO2, 5M aq. HNO3 / 0.5 h / 70 - 75 °C 3: thionyl chloride / 1.) room temp., 8 h, 2.) 100 deg C, 0.5 h 4: diethyl ether / 1.) RT, 2 h, 2.) reflux, 2 h View Scheme
Multi-step reaction with 3 steps 1.1: potassium tert-butylate / tetrahydrofuran / 0 °C 1.2: 12 h / 0 - 20 °C 2.1: sodium nitrite; nitric acid / water / 0.58 h / 75 °C 3.1: triethylamine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate / N,N-dimethyl-formamide / 2 h / 20 °C / Schlenk technique View Scheme

: 121-33-5
vanillin

KOH-solution: KOH-solution

: 404-86-4
capsaicin

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: ammonium formate / 3 h / 180 °C 2: diethyl ether / 1.) RT, 2 h, 2.) reflux, 2 h View Scheme

: 31467-60-4
(6Z)-8-methyl-6-nonaneneoic acid

: 404-86-4
capsaicin

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 2M NaNO2, 5M aq. HNO3 / 0.5 h / 70 - 75 °C 2: thionyl chloride / 1.) room temp., 8 h, 2.) 100 deg C, 0.5 h 3: diethyl ether / 1.) RT, 2 h, 2.) reflux, 2 h View Scheme
Multi-step reaction with 2 steps 1: sodium nitrite; nitric acid / water / 0.58 h / 75 °C 2: triethylamine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate / N,N-dimethyl-formamide / 2 h / 20 °C / Schlenk technique View Scheme

: 502-44-3
hexahydro-2H-oxepin-2-one

: 404-86-4
capsaicin

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: conc. H2SO4 / Heating 2: pyridinium chlorochromate (PCC), sodium acetate / CH2Cl2 / 1.5 h / Ambient temperature 4: Na(Hg), MeOH / tetrahydrofuran / 8 h / -20 °C 5: aq. KOH / ethanol / 1 h / Heating 6: thionyl chloride / 1.) RT, 18 h, 2.) 100 deg C, 30 min 7: diethyl ether / 72 h / Ambient temperature View Scheme

: 6654-36-0
methyl 6-oxohexanoate

: 404-86-4
capsaicin

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 2: Na(Hg), MeOH / tetrahydrofuran / 8 h / -20 °C 3: aq. KOH / ethanol / 1 h / Heating 4: thionyl chloride / 1.) RT, 18 h, 2.) 100 deg C, 30 min 5: diethyl ether / 72 h / Ambient temperature View Scheme

: 4547-43-7
methyl 6-hydroxycaproate

: 404-86-4
capsaicin

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: pyridinium chlorochromate (PCC), sodium acetate / CH2Cl2 / 1.5 h / Ambient temperature 3: Na(Hg), MeOH / tetrahydrofuran / 8 h / -20 °C 4: aq. KOH / ethanol / 1 h / Heating 5: thionyl chloride / 1.) RT, 18 h, 2.) 100 deg C, 30 min 6: diethyl ether / 72 h / Ambient temperature View Scheme

: Benzoic acid 1-(1-benzenesulfonyl-2-methyl-propyl)-5-methoxycarbonyl-pentyl ester

: 404-86-4
capsaicin

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: Na(Hg), MeOH / tetrahydrofuran / 8 h / -20 °C 2: aq. KOH / ethanol / 1 h / Heating 3: thionyl chloride / 1.) RT, 18 h, 2.) 100 deg C, 30 min 4: diethyl ether / 72 h / Ambient temperature View Scheme

: 5631-95-8
2,3-dichlorotetrahydro-2H-pyran

: 404-86-4
capsaicin

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: diethyl ether 2: sodium; diisopropyl ether 3: pyridine; phosphorus (III)-bromide 4: ethanol / und Erwaermen des Reaktionsprodukts mit wss.Kalilauge und Erhitzen des nach dem Ansaeuern isolierten Reaktionsprodukts bis auf 180grad 5: SOCl2 / Behandeln des Reaktionsprodukts mit 4-Aminomethyl-2-methoxy-phenol in Aether View Scheme

: 59721-81-2
3-chloro-2-isopropyltetrahydropyran

: 404-86-4
capsaicin

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: sodium; diisopropyl ether 2: pyridine; phosphorus (III)-bromide 3: ethanol / und Erwaermen des Reaktionsprodukts mit wss.Kalilauge und Erhitzen des nach dem Ansaeuern isolierten Reaktionsprodukts bis auf 180grad 4: SOCl2 / Behandeln des Reaktionsprodukts mit 4-Aminomethyl-2-methoxy-phenol in Aether View Scheme

: 59721-83-4
(E)-7-bromo-2-methyl-3-heptene

: 404-86-4
capsaicin

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: ethanol / und Erwaermen des Reaktionsprodukts mit wss.Kalilauge und Erhitzen des nach dem Ansaeuern isolierten Reaktionsprodukts bis auf 180grad 2: SOCl2 / Behandeln des Reaktionsprodukts mit 4-Aminomethyl-2-methoxy-phenol in Aether View Scheme

: C44H75NO12P(1-)*Na(1+)

: 404-86-4
capsaicin

Conditions

Conditions	Yield
With ethylenediaminetetraacetic acid; secretory phospholipase A2 from venom of Agkistrodon piscivorus piscivorus; potassium chloride; calcium chloride at 50℃; pH=7.5; aq. buffer;

: 1221557-61-4
N-[(6-bromo-7-hydroxycoumarin-4-yl)methoxycarbonyl]dopamine

A: 404-86-4
capsaicin

B: 223420-41-5
6-bnromo-7-hydroxy-4-(hydroxymethyl)-2H-chromen-2-one

Conditions

Conditions	Yield
With water Photolysis;

: 1221557-70-5
(E)-[8-[bis(carboxymethyl)aminomethyl]-6-bromo-7-hydroxycoumarin-4-yl]methyl 2-methoxy-4-[(8-methylnon-6-enamido)methyl]phenyl carbonate

A: 1221557-66-9
8-[bis(carboxymethyl)aminomethyl]-6-bromo-7-hydroxy-4-(hydroxymethyl)coumarin

B: 404-86-4
capsaicin

Conditions

Conditions	Yield
With water Photolysis;

: 498-00-0
4-hydroxymethyl-2-methoxyphenol

: 404-86-4
capsaicin

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: oxygen / toluene / 3 h / 70 °C / Sealed tube 2.1: D-glucose; L-alanin; ammonium chloride; glucose dehydrogenase; amine transaminase; L-alanine dehydrogenase; NADH; sodium hydroxide / dimethyl sulfoxide / 22 h / 37 °C / pH 8.2 / Darkness; Enzymatic reaction 3.1: sodium hydrogencarbonate / water; chloroform / 0.75 h / 20 °C 3.2: 1 h / 20 - 40 °C View Scheme
Multi-step reaction with 3 steps 1: oxygen / toluene / 3 h / 70 °C / Sealed tube 2: D-glucose; L-alanin; ammonium chloride; glucose dehydrogenase; amine transaminase; L-alanine dehydrogenase; NADH; sodium hydroxide / dimethyl sulfoxide / 22 h / 37 °C / pH 8.2 / Darkness; Enzymatic reaction 3: lipase / tert-Amyl alcohol / 48 h / 45 °C / Molecular sieve; Enzymatic reaction View Scheme
Multi-step reaction with 4 steps 1.1: oxygen / toluene / 3 h / 70 °C / Sealed tube 2.1: rac-Pro-OH / 24 h / 20 °C / Inert atmosphere 3.1: D-glucose; L-alanin; ammonium chloride; glucose dehydrogenase; amine transaminase; L-alanine dehydrogenase; NADH; sodium hydroxide / dimethyl sulfoxide / 90 h / 37 °C / pH 8.2 / Darkness; Enzymatic reaction 4.1: sodium hydrogencarbonate / water; chloroform / 0.75 h / 20 °C 4.2: 1 h / 20 - 40 °C View Scheme
Multi-step reaction with 4 steps 1: oxygen / toluene / 3 h / 70 °C / Sealed tube 2: rac-Pro-OH / 24 h / 20 °C / Inert atmosphere 3: D-glucose; L-alanin; ammonium chloride; glucose dehydrogenase; amine transaminase; L-alanine dehydrogenase; NADH; sodium hydroxide / dimethyl sulfoxide / 90 h / 37 °C / pH 8.2 / Darkness; Enzymatic reaction 4: lipase / tert-Amyl alcohol / 48 h / 45 °C / Molecular sieve; Enzymatic reaction View Scheme

: 1196-92-5
Vanillylamin

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

: 404-86-4
capsaicin

Conditions

Conditions	Yield
With lipase In tert-Amyl alcohol at 45℃; for 48h; Molecular sieve; Enzymatic reaction;

: 61152-59-8
4-(4-hydroxyphenyl-3-methoxy)-4-hydroxy-2-butanone

: 404-86-4
capsaicin

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: D-glucose; L-alanin; ammonium chloride; glucose dehydrogenase; amine transaminase; L-alanine dehydrogenase; NADH; sodium hydroxide / dimethyl sulfoxide / 90 h / 37 °C / pH 8.2 / Darkness; Enzymatic reaction 2.1: sodium hydrogencarbonate / water; chloroform / 0.75 h / 20 °C 2.2: 1 h / 20 - 40 °C View Scheme
Multi-step reaction with 2 steps 1: D-glucose; L-alanin; ammonium chloride; glucose dehydrogenase; amine transaminase; L-alanine dehydrogenase; NADH; sodium hydroxide / dimethyl sulfoxide / 90 h / 37 °C / pH 8.2 / Darkness; Enzymatic reaction 2: lipase / tert-Amyl alcohol / 48 h / 45 °C / Molecular sieve; Enzymatic reaction View Scheme

: 121-33-5
vanillin

: 404-86-4
capsaicin

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: D-glucose; L-alanin; ammonium chloride; glucose dehydrogenase; amine transaminase; L-alanine dehydrogenase; NADH; sodium hydroxide / dimethyl sulfoxide / 22 h / 37 °C / pH 8.2 / Darkness; Enzymatic reaction 2.1: sodium hydrogencarbonate / water; chloroform / 0.75 h / 20 °C 2.2: 1 h / 20 - 40 °C View Scheme
Multi-step reaction with 2 steps 1: D-glucose; L-alanin; ammonium chloride; glucose dehydrogenase; amine transaminase; L-alanine dehydrogenase; NADH; sodium hydroxide / dimethyl sulfoxide / 22 h / 37 °C / pH 8.2 / Darkness; Enzymatic reaction 2: lipase / tert-Amyl alcohol / 48 h / 45 °C / Molecular sieve; Enzymatic reaction View Scheme
Multi-step reaction with 3 steps 1.1: rac-Pro-OH / 24 h / 20 °C / Inert atmosphere 2.1: D-glucose; L-alanin; ammonium chloride; glucose dehydrogenase; amine transaminase; L-alanine dehydrogenase; NADH; sodium hydroxide / dimethyl sulfoxide / 90 h / 37 °C / pH 8.2 / Darkness; Enzymatic reaction 3.1: sodium hydrogencarbonate / water; chloroform / 0.75 h / 20 °C 3.2: 1 h / 20 - 40 °C View Scheme
Multi-step reaction with 3 steps 1: rac-Pro-OH / 24 h / 20 °C / Inert atmosphere 2: D-glucose; L-alanin; ammonium chloride; glucose dehydrogenase; amine transaminase; L-alanine dehydrogenase; NADH; sodium hydroxide / dimethyl sulfoxide / 90 h / 37 °C / pH 8.2 / Darkness; Enzymatic reaction 3: lipase / tert-Amyl alcohol / 48 h / 45 °C / Molecular sieve; Enzymatic reaction View Scheme

: 404-86-4
capsaicin

: 141-75-3
butyryl chloride

: 4-[((6E)-8-methylnon-6-enoylamino)methyl]-2-methyoxyphenyl butanoate

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 2h;	96%
With triethylamine In dichloromethane at 20℃; for 13 - 21h; dark; Heating / reflux;	95%
With triethylamine In dichloromethane at 20 - 45℃; for 24 - 32h; Heating / reflux;	95%
With triethylamine In dichloromethane at 20℃; Reflux;	95%

: 404-86-4
capsaicin

: 112-76-5
Stearoyl chloride

: 4-[((6E)-8-methylnon-6-enoylamino)methyl]-2-methyoxyphenyl octadecanoate

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 2h;	96%

: 404-86-4
capsaicin

: 112-67-4
n-hexadecanoyl chloride

: capsaicin palmitate

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 40℃; Darkness; Reflux; Large scale;	95%
With triethylamine; dmap In dichloromethane at 20℃; for 13 - 21h; Heating / reflux;	95%

: 404-86-4
capsaicin

: 79-03-8
propionyl chloride

: 4-[((6E)-8-methylnon-6-enoylamino)methyl]-2-methyoxyphenyl propanoate

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 2h;	94%

: 404-86-4
capsaicin

: N-(4-methoxybenzyl)benzenesulfonimidoyl fluoride

: 18162-48-6
tert-butyldimethylsilyl chloride

: (E)-2-methoxy-4-((8-methylnon-6-enamido)methyl)phenyl N-(4-methoxybenzyl)benzene sulfonimidate

Conditions

Conditions	Yield
Stage #1: capsaicin With 1H-imidazole In dichloromethane at 20℃; for 0.0833333h; Stage #2: tert-butyldimethylsilyl chloride In dichloromethane at 20℃; for 5h; Stage #3: N-(4-methoxybenzyl)benzenesulfonimidoyl fluoride With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane; acetonitrile at 60℃; for 10h; Sealed tube; Inert atmosphere;	94%

...Expand

: 404-86-4
capsaicin

: 19408-84-5
dihydrocapsaicin

Conditions

Conditions	Yield
With triethylsilane; 1% Pd on activated carbon In water at 45℃; for 12h; Reagent/catalyst; Green chemistry; chemoselective reaction;	93%
With platinum (IV) oxide hydrate; hydrogen In methanol at 20℃; under 760.051 Torr; for 7h; Solvent;	85%
With hydrogen; palladium on activated charcoal In ethanol under 760 Torr; for 4h;

: 404-86-4
capsaicin

: 3282-30-2
pivaloyl chloride

: 4-[((6E)-8-methylnon-6-enoylamino)methyl]-2-methyoxyphenyl 2,2-dimethylpropanoate

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 2h;	92.5%

: 404-86-4
capsaicin

: 138500-85-3
4-bromomethylphenylboronic acid pinacol ester

: C31H44BNO5

Conditions

Conditions	Yield
With potassium carbonate In acetone at 60℃; for 2h;	90.5%

: 404-86-4
capsaicin

: 79-04-9
chloroacetyl chloride

: 1236876-87-1
(E)-2-methoxy-4-((8-methylnon-6-enamido)methyl)phenyl 2-chloroacetate

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 1h;	90.3%

: 14602-86-9
(1R,2S,5R)-menthyl chloroformate

: 404-86-4
capsaicin

: 913290-19-4
(1S,2S,5R)-5-methyl-2-(methylethyl)cyclohexyl {4-[((6E)-8-methylnon-6-enoylamino)methyl]-2-methyoxyphenoxy}formate

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 2h;	87%

: 404-86-4
capsaicin

: 503-38-8
trichloromethyl chloroformate

: 913290-18-3
4-[((6E)-8-methylnon-6-enoylamino)methyl]-2-methyoxyphenyl {4-[((6E)-8-methylnon-6-enoylamino)methyl]-2-methoxyphenoxy}formate

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 3h;	86.5%

: 404-86-4
capsaicin

: 75-36-5
acetyl chloride

: O-acetylcapsaicin

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 2h;	86%

: 404-86-4
capsaicin

: 4-cyano-N,N,N-trimethylanilinium trifluoromethansulfonate

: C25H30N2O3

Conditions

Conditions	Yield
Stage #1: capsaicin With potassium tert-butylate In tetrahydrofuran; N,N-dimethyl-formamide at 25℃; for 0.166667h; Inert atmosphere; Schlenk technique; Stage #2: 4-cyano-N,N,N-trimethylanilinium trifluoromethansulfonate In tetrahydrofuran; N,N-dimethyl-formamide at 25℃; for 3h; Inert atmosphere; Schlenk technique;	83%

: dimethyl-4-nitrophenylsulfonium trifluoromethanesulfonate

: 404-86-4
capsaicin

: (E)-N-(3-methoxy-4-(4-nitrophenoxy)benzyl)-8-methylnon-6-enamide

Conditions

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 3h; Inert atmosphere; Schlenk technique;	83%

: 64-18-6
formic acid

: 404-86-4
capsaicin

: 913290-13-8
4-[((6E)-8-methylnon-6-enoylamino)methyl]-2-methyoxyphenyl formate

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 4h;	80.2%

: 763-32-6
2-methyl-1-buten-4-ol

: 404-86-4
capsaicin

: C23H35NO3

Conditions

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran; toluene for 1.5h; Inert atmosphere; Reflux;	79%

: 1-(prop-1-yn-1-yl)-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one

: 404-86-4
capsaicin

: C28H34INO5

Conditions

Conditions	Yield
With caesium carbonate In ethanol at 20℃; chemoselective reaction;	77%

: 404-86-4
capsaicin

: 96-34-4
methyl chloroacetate

: {2-Methoxy-4-[(8-methyl-non-6-enoylamino)-methyl]-phenoxy}-acetic acid methyl ester

Conditions

Conditions	Yield
With disodium hydrogenphosphate; potassium carbonate; sodium iodide In acetone for 6h; Heating / reflux;	71.4%
With disodium hydrogenphosphate; potassium carbonate; sodium iodide In acetone for 6h; Heating / reflux;	71.4%

: 404-86-4
capsaicin

: N-ethylmethylalanine

: (E)-2-methoxy-4-((8-methylnon-6-enamido)methyl)phenyl N-ethyl-N-methylalanine hydrochloride

Conditions

Conditions	Yield
Stage #1: capsaicin; N-ethylmethylalanine With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at -5 - 20℃; for 2h; Stage #2: With hydrogenchloride In ethyl acetate at 20℃; for 1h; pH=3 - 4;	70.2%

: 404-86-4
capsaicin

: 58685-78-2
1-carboxy-N,N-dimethyl-1-phenylmethanaminiumchloride

: C28H38N2O4*ClH

Conditions

Conditions	Yield
Stage #1: capsaicin; 1-carboxy-N,N-dimethyl-1-phenylmethanaminiumchloride With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at -5 - 20℃; for 2h; Stage #2: With hydrogenchloride In ethyl acetate at 20℃; for 1h; pH=3 - 4;	68.2%

: 404-86-4
capsaicin

: 2-([1,4'-bipiperidin]-1'-yl)propionic acid hydrochloride

: C31H49N3O4*ClH

Conditions

Conditions	Yield
Stage #1: capsaicin; 2-([1,4'-bipiperidin]-1'-yl)propionic acid hydrochloride With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at -5 - 20℃; for 2h; Stage #2: With hydrogenchloride In ethyl acetate at 20℃; for 1h; pH=3 - 4;	63.2%

: 404-86-4
capsaicin

: N,N-diethyl-L-isoleucine

: C28H46N2O4*ClH

Conditions

Conditions	Yield
Stage #1: capsaicin; N,N-diethyl-L-isoleucine With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at -5 - 20℃; for 2h; Stage #2: With hydrogenchloride In ethyl acetate at 20℃; for 1h; pH=3 - 4;	60.5%

: 4530-20-5
BOC-glycine

: 404-86-4
capsaicin

: C25H38N2O6

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at -5 - 20℃; for 2h;	60.5%

: N-ethyl-N-methyl-glycine

: 404-86-4
capsaicin

: (E)-2-methoxy-4-((8-methylnon-6-enamido)methyl)phenyl N-ethyl-N-methylglycine hydrochloride

Conditions

Conditions	Yield
Stage #1: N-ethyl-N-methyl-glycine; capsaicin With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at -5 - 20℃; for 2h; Stage #2: With hydrogenchloride In ethyl acetate at 20℃; for 1h; pH=3 - 4;	60.1%

: 404-86-4
capsaicin

: 134386-10-0
N,N'-(3,3'-Bi-4-hydroxy-5-methoxybenzyl)di-8-methylnon-(E)-6-enamide

Conditions

Conditions	Yield
With riboflavin In ethanol at 30℃; for 0.333333h; Irradiation; pH 5.0 (citrate buffer);	60%
With Capsicum annuum var. annuum cell protein extract; dihydrogen peroxide In water at 30℃; for 1.25h; pH=7.0;
With dihydrogen peroxide; horseradish peroxidase In aq. buffer at 20℃; for 0.166667h; pH=5.5;

: 404-86-4
capsaicin

: N-ethyl-N-isopropylglycine

: (E)-2-methoxy-4-((8-methylnon-6-enoylamino)methyl)phenyl N-ethyl-N-isopropylglycine hydrochloride

Conditions

Conditions	Yield
Stage #1: capsaicin; N-ethyl-N-isopropylglycine With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at -5 - 20℃; for 2h; Stage #2: With hydrogenchloride In ethyl acetate at 20℃; for 1h; pH=3 - 4;	59.3%

: 404-86-4
capsaicin

: 4989-36-0
4-carbamothioylbenzoic acid

: (E)-2-methoxy-4-((8-methylnon-6-enamido)methyl)phenyl 4-carbamothioyl benzoate

Conditions

Conditions	Yield
Stage #1: capsaicin With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 0.333333h; Stage #2: 4-thiocarbamoylbenzoic acid In dichloromethane	57.3%

: 22071-15-4
ketoprofen

: 404-86-4
capsaicin

: 1224428-97-0
2-(3-benzoyl-phenyl)-propionic acid 2-methoxy-4-[(8-methylnon-6-enoylamino)-methyl]-phenyl ester

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 30 - 35℃;	56.6%

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

Product Name

Capsaicin

Synthetic route

Capsaicin Chemical Properties

Capsaicin History

Capsaicin Uses

Capsaicin Toxicity Data With Reference

Capsaicin Safety Profile

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