CAS No.25775-90-0,(Z)-CAPSAICIN Suppliers

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Basic Information

Molecular Structure:
CAS No.:	25775-90-0
Name:	(Z)-CAPSAICIN
Article Data:	4

Formula:	C₁₈H₂₇NO₃
Molecular Weight:	305.417
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;
EINECS:	206-969-8
Density:	1.042 g/cm³
Melting Point:	70 °C
Boiling Point:	511.462 °C at 760 mmHg
Flash Point:	263.123 °C
PSA:	58.56000
LogP:	4.18050

Synthetic route

: 1196-92-5
Vanillylamin

: 31467-61-5
(Z)-8-Methyl-non-6-enoyl chloride

: 25775-90-0
cis-capsaicin

Conditions

Conditions	Yield
In diethyl ether; N,N-dimethyl-formamide	70%
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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%

...Expand

: 25775-90-0
cis-capsaicin

: 19408-84-5
dihydrocapsaicin

Conditions

Conditions	Yield
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

Conditions	Yield
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

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

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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.