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(Z)-Capsaicin
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Name

(Z)-Capsaicin

 EINECS 206-969-8
CAS No. 25775-90-0 Density 1.042 g/cm3
PSA 58.56000 LogP 4.18050
Solubility N/A Melting Point 70 °C
Formula C18H27NO3 Boiling Point 511.462 °C at 760 mmHg
Molecular Weight 305.417 Flash Point 263.123 °C
Transport Information N/A Appearance N/A
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 25775-90-0 ((Z)-CAPSAICIN) Hazard Symbols N/A
Synonyms

6-Nonenamide,8-methyl-N-vanillyl-, (Z)- (8CI);6-Nonenamide, N-[(4-hydroxy-3-methoxyphenyl)methyl]-8-methyl-,(Z)-;(Z)-8-Methyl-N-vanillyl-6-nonenamide;Capsaicin, cis-;Civamide;Zucapsaicin;cis-Capsaicin;

Article Data 4

(Z)-Capsaicin Synthetic route

1196-92-5

Vanillylamin

31467-61-5

(Z)-8-Methyl-non-6-enoyl chloride

25775-90-0

cis-capsaicin

Conditions
ConditionsYield
In diethyl ether; N,N-dimethyl-formamide70%
In diethyl ether for 72h; Ambient temperature;
In diethyl ether 1.) room temp., 2 h, 2.) reflux, 2 h; Yield given;
In tert-butyl methyl ether at 20 - 40℃; for 4h;5.42 g
31467-60-4

(6Z)-8-methyl-6-nonaneneoic acid

25775-90-0

cis-capsaicin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: oxalyl chloride / 3 h
2: 70 percent / dimethylformamide; diethyl ether
View Scheme
Multi-step reaction with 2 steps
1: thionyl chloride / 1.) RT, 8 h, 2.) 100 deg C, 0.5 h
2: diethyl ether / 1.) room temp., 2 h, 2.) reflux, 2 h
View Scheme
Multi-step reaction with 2 steps
1: thionyl chloride / 1.) RT, 18 h, 2.) 100 deg C, 30 min
2: diethyl ether / 72 h / Ambient temperature
View Scheme
50889-29-7

(5-carboxypentyl)triphenylphosphonium bromide

25775-90-0

cis-capsaicin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: t-BuOK / dimethylformamide / 15 h / Ambient temperature
2: thionyl chloride / 1.) RT, 8 h, 2.) 100 deg C, 0.5 h
3: diethyl ether / 1.) room temp., 2 h, 2.) reflux, 2 h
View Scheme
121-33-5

vanillin

KOH-solution

KOH-solution

25775-90-0

cis-capsaicin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: ammonium formate / 3 h / 180 °C
2: diethyl ether / 1.) room temp., 2 h, 2.) reflux, 2 h
View Scheme
502-44-3

hexahydro-2H-oxepin-2-one

25775-90-0

cis-capsaicin

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: conc. H2SO4 / Heating
2: pyridinium chlorochromate (PCC), sodium acetate / CH2Cl2 / 1.5 h / Ambient temperature
3: 1.) t-BuOK / 1.) DMF, RT, 5 min, 2.) a) RT, 20 h, b) 90 deg C, 1 h
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
6654-36-0

methyl 6-oxohexanoate

25775-90-0

cis-capsaicin

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 1.) t-BuOK / 1.) DMF, RT, 5 min, 2.) a) RT, 20 h, b) 90 deg C, 1 h
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
24424-99-5

di-tert-butyl dicarbonate

69739-34-0

t-butyldimethylsiyl triflate

25775-90-0

cis-capsaicin

(Z)-tert-butyl 4-(tert-butyldimethylsilyloxy)-3-methoxybenzyl(8-methylnon-6-enoyl)carbamate

Conditions
ConditionsYield
Stage #1: t-butyldimethylsiyl triflate; cis-capsaicin With triethylamine In dichloromethane at 0 - 22℃; for 0.5h;
Stage #2: di-tert-butyl dicarbonate With dmap In dichloromethane; acetonitrile at 22℃; for 1h;		76%
25775-90-0

cis-capsaicin

19408-84-5

dihydrocapsaicin

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In ethanol under 760 Torr; for 4h;
25775-90-0

cis-capsaicin

(Z)-tert-butyl 4-(tert-butyldimethylsilyloxy)-3-methoxybenzyl(8,8,8-trifluorooct-6-enoyl)carbamate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: triethylamine / dichloromethane / 0.5 h / 0 - 22 °C
2: dmap / acetonitrile / 1 h / 22 °C
3: C47H71ClMoN2O / benzene / 4 h / 22 °C / Glovebox; Inert atmosphere
View Scheme
25775-90-0

cis-capsaicin

(Z)-tert-butyl 4-(tert-butyldimethylsilyloxy)-3-methoxybenzyl(8-methylnon-6-enoyl)carbamate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: triethylamine / dichloromethane / 0.5 h / 0 - 22 °C
2: dmap / acetonitrile / 1 h / 22 °C
View Scheme

(Z)-Capsaicin Specification

The (Z)-Capsaicin, with the CAS registry number 25775-90-0, is also known as (Z)-8-Methyl-N-vanillyl-6-nonenamide. It belongs to the product categories of Anilines, Aromatic Amines and Nitro Compounds; Vanilloid/TRPV channel; Amines; Aromatics; Intermediates & Fine Chemicals; Pharmaceuticals. This chemical's molecular formula is C18H27NO3 and molecular weight is 305.41. What's more, its systematic name is (6Z)-N-(4-Hydroxy-3-methoxybenzyl)-8-methyl-6-nonenamide. Its classification codes are: (1)Analgesic [topical]; (2)Drug / Therapeutic Agent. This chemical is the cis-isomer of alkyl vanillylamide.

Physical properties of (Z)-Capsaicin are: (1)ACD/LogP: 3.327; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.33; (4)ACD/LogD (pH 7.4): 3.33; (5)ACD/BCF (pH 5.5): 198.94; (6)ACD/BCF (pH 7.4): 198.07; (7)ACD/KOC (pH 5.5): 1538.22; (8)ACD/KOC (pH 7.4): 1531.50; (9)#H bond acceptors: 4; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 10; (12)Polar Surface Area: 58.56 Å2; (13)Index of Refraction: 1.524; (14)Molar Refractivity: 89.699 cm3; (15)Molar Volume: 293.171 cm3; (16)Polarizability: 35.559×10-24cm3; (17)Surface Tension: 38.7 dyne/cm; (18)Density: 1.042 g/cm3; (19)Flash Point: 263.123 °C; (20)Enthalpy of Vaporization: 81.201 kJ/mol; (21)Boiling Point: 511.462 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(NCc1cc(OC)c(O)cc1)CCCC\C=C/C(C)C
(2)Std. InChI: 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-
(3)Std. InChIKey: YKPUWZUDDOIDPM-VURMDHGXSA-N

The toxicity data is as follows:  

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 25mg/kg (25mg/kg)   Journal of Medicinal Chemistry. Vol. 36, Pg. 2595, 1993.

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