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7553-53-9 molecular structure
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(6E)-N-[(4-hydroxy-3-methoxyphenyl)methyl]-8-methylnon-6-enamide

ChemBase ID: 72832
Molecular Formular: C18H27NO3
Molecular Mass: 305.41188
Monoisotopic Mass: 305.19909373
SMILES and InChIs

SMILES:
c1(c(cc(cc1)CNC(=O)CCCC/C=C/C(C)C)OC)O
Canonical SMILES:
COc1cc(CNC(=O)CCCC/C=C/C(C)C)ccc1O
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+
InChIKey:
YKPUWZUDDOIDPM-SOFGYWHQSA-N

Cite this record

CBID:72832 http://www.chembase.cn/molecule-72832.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(6E)-N-[(4-hydroxy-3-methoxyphenyl)methyl]-8-methylnon-6-enamide
N-[(4-hydroxy-3-methoxyphenyl)methyl]-8-methylnon-6-enamide
IUPAC Traditional name
capsaicin
N-[(4-hydroxy-3-methoxyphenyl)methyl]-8-methylnon-6-enamide
(6E)-N-[(4-hydroxy-3-methoxyphenyl)methyl]-8-methylnon-6-enamide
Synonyms
Qutenza
Vanilloid
Capsaicin(Qutenza)
CAPSAICIN, NATURAL
8-Methyl-N-vanillyl-trans-6-nonenamide
N-[(4-Hydroxy-3-methoxyphenyl)methyl]-8-methyl-6-nonenamide
(E/Z)-8-Methyl-N-vanillyl-6-nonenamide
Capsaicin(E/Z-Mixture)
(6E)-N-[(4-hydroxy-3-methoxyphenyl)methyl]-8-methyl-6-nonenamide
(E)-8-Methyl-N-vanillyl-6-nonenamide
(E)-N-(4-Hydroxy-3-methoxybenzyl)-8-methylnon-6-enamide
ALGRX 4975
Adlea
Axsain
Capsaicine
Capsin P 50
Capzasin-HP
Dolenon
E-Capsaicin
Mioton
N-(4-Oxy-3-methoxybenzyl)-8-methyl-6-nonenamide
NGX 4010
NSC 56353
Ovocap
Ratden PE 40
Togarashi Orenji
Zostrix
trans-8-Methyl-N-vanillyl-6-nonenamide
trans-Capsaicin
Capsaicin
(E)-N-(4-hydroxy-3-methoxybenzyl)-8-methylnon-6-enamide
(E)-N-(4-Hydroxy-3-methoxybenzyl)
-8-methylnon-6-enamide
trans-8-Methyl-N-vanillylnon
-6-enamide
(E)-Capsaicin
Capsicine
Capsicin
CPS
Capsaicin
Capsaicin
8-METHYL-N-VANILLYL-6-NONENAMIDE
Natural capsaicin
Capsacutin
Capsaiene
8-甲基-N-香草基-反-6-壬烯酰胺
辣椒碱
CAS Number
7553-53-9
404-86-4
EC Number
206-969-8
MDL Number
MFCD00017259
Beilstein Number
2816484
PubChem SID
24862158
24847432
24853015
24896598
162037753
PubChem CID
1548943
CHEBI ID
3374
ATC CODE
N01BX04
M02AB01
CHEMBL
294199
Chemspider ID
1265957
KEGG ID
C06866
Unique Ingredient Identifier
S07O44R1ZM
Wikipedia Title
Capsaicin

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 9.928692  H Acceptors
H Donor LogD (pH = 5.5) 3.749653 
LogD (pH = 7.4) 3.7483943  Log P 3.7496696 
Molar Refractivity 90.3174 cm3 Polarizability 34.670914 Å3
Polar Surface Area 58.56 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
.0013 g/100 mL in water expand Show data source
Chloroform expand Show data source
DMSO expand Show data source
ethanol: soluble expand Show data source
H2O: insoluble expand Show data source
Methanol expand Show data source
soluble in alcohol, ether, benzene
slightly soluble in CS2. HCl, petroleum
expand Show data source
Apperance
Off-White to Pale Yellow Solid expand Show data source
pure dark red solid expand Show data source
Melting Point
60-62°C expand Show data source
62 - 65°C expand Show data source
62-65 °C expand Show data source
62-65 °C(lit.) expand Show data source
62-65°C expand Show data source
Boiling Point
210 - 220°C (0.01 Torr) expand Show data source
210-212°C expand Show data source
Flash Point
113 °C expand Show data source
235.4 °F expand Show data source
Odor
highly volatile and pungent expand Show data source
Storage Condition
-20°C expand Show data source
-20°C Freezer, Under Inert Atmosphere expand Show data source
2-8°C expand Show data source
RTECS
RA8530000 expand Show data source
European Hazard Symbols
Toxic Toxic (T) expand Show data source
UN Number
2811 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Hazard Class
6.1 expand Show data source
Packing Group
2 expand Show data source
II expand Show data source
Australian Hazchem
2XE expand Show data source
Risk Statements
25-37/38-41-42/43 expand Show data source
R:25 expand Show data source
R24/25 expand Show data source
Safety Statements
22-26-28-36/39-45 expand Show data source
S:28-36/37/39-45-53 expand Show data source
S26, S36/37/39, S45 expand Show data source
EU Classification
T2 expand Show data source
EU Hazard Identification Number
6.1B expand Show data source
Emergency Response Guidebook(ERG) Number
154 expand Show data source
GHS Pictograms
GHS05 expand Show data source
GHS06 expand Show data source
GHS08 expand Show data source
GHS Signal Word
Danger expand Show data source
Main Hazard
Toxic (T) expand Show data source
NFPA704
NFPA 704 diagram
1
2
0
expand Show data source
GHS Hazard statements
H301-H315-H317-H318-H334-H335 expand Show data source
GHS Precautionary statements
P261-P280-P301 + P310-P305 + P351 + P338-P342 + P311 expand Show data source
Personal Protective Equipment
Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges expand Show data source
RID/ADR
UN 2811 6.1/PG 2 expand Show data source
Storage Temperature
2-8°C expand Show data source
Target
vasopressin receptor expand Show data source
Gene Information
human ... CYP1A2(1544), TRPV1(7442)rat ... Trpv1(83810), Trpv4(66026) expand Show data source
Mechanism of Action
Gastric motility inhibitor expand Show data source
Prevents reaccumulation of substance-P in peripheral sensory neurons expand Show data source
Probable mechanism: substance-P-depletor expand Show data source
Purity
~60% expand Show data source
>90% expand Show data source
≥50% (HPLC) expand Show data source
≥95% expand Show data source
≥99.0% (HPLC) expand Show data source
65-70% expand Show data source
Grade
natural expand Show data source
Salt Data
Free Base expand Show data source
Compostion
capsaicin, 65% expand Show data source
dihydrocapsaicin, 35% expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Description
Isomers expand Show data source
Impurities
~35% dihydrocapsaicin expand Show data source
Biological Source
from Capsicum sp. expand Show data source
Pungent principle of various Capsicum spp. (Solanaceae) expand Show data source
Application(s)
Irritant used for desensitisation of sensory neurones expand Show data source
Used as a counterirritant and topical analgesic for some skin conditions expand Show data source
Used as a selective probe for studying neurogenic inflammation and the role of nociceptors in human physiol expand Show data source
Linear Formula
(CH3)2CHCH=CH(CH2)4CONHCH2C6H3-4-(OH)-3-(OCH3) expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals Selleck Chemicals Selleck Chemicals InterBioScreen InterBioScreen Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich TRC TRC
MP Biomedicals - 02199516 external link
Synthetic (Natural compound obtained by total synthesis)
Assay(HPLC): >90%
Topical Analgesic(for neuralgia).
MP Biomedicals - 02190239 external link
Purity: 65-70%
Contains up to 30-35% <->Dihydro analog
Induces substance P release from afferent nociceptive specific neurons.
Selleck Chemicals - S1990 external link
Research Area: Neurological Disease
Biological Activity:
Capsaicin is an active component of chili peppers, which are plants belonging to the genus Capsicum. The burning and painful sensations associated with capsaicin result from its chemical interaction with sensory neurons. Capsaicin, as a member of the vanilloid family, binds to a receptor called the vanilloid receptor subtype 1 (VR1). By binding to the VR1 receptor, the capsaicin molecule produces the same sensation that excessive heat or abrasive damage would cause, explaining why the spiciness of capsaicin is described as a burning sensation. [1]
Sigma Aldrich - M2028 external link
Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Biochem/physiol Actions
Prototype vanilloid receptor agonist. Neurotoxin; activates sensory neurons that give rise to unmyelinated C-fibers, many of which contain substance P. Topical application desensitizes the sensory nerve endings giving a paradoxical antinociceptive effect; systemic administration can be neurotoxic to capsaicin-sensitive cells, especially in newborn animals. Active component of chili peppers.
Sigma Aldrich - 21750 external link
Packaging
1, 5 g in glass bottle
100 mg in glass bottle
Biochem/physiol Actions
Prototype vanilloid receptor agonist. Neurotoxin; activates sensory neurons that give rise to unmyelinated C-fibers, many of which contain substance P. Topical application desensitizes the sensory nerve endings giving a paradoxical antinociceptive effect; systemic administration can be neurotoxic to capsaicin-sensitive cells, especially in newborn animals. Active component of chili peppers.
Sigma Aldrich - 360376 external link
Packaging
1 g in glass bottle
250 mg in glass bottle
Biochem/physiol Actions
Prototype vanilloid receptor agonist. Neurotoxin; activates sensory neurons that give rise to unmyelinated C-fibers, many of which contain substance P. Topical application desensitizes the sensory nerve endings giving a paradoxical antinociceptive effect; systemic administration can be neurotoxic to capsaicin-sensitive cells, especially in newborn animals. Active component of chili peppers.
Sigma Aldrich - M3403 external link
Quality
Contains approx. 30% dihydrocapsaicin, balance other naturally occurring capsaicinoids.
Biochem/physiol Actions
Prototype vanilloid receptor agonist. Neurotoxin; activates sensory neurons that give rise to unmyelinated C-fibers, many of which contain substance P. Topical application desensitizes the sensory nerve endings giving a paradoxical antinociceptive effect; systemic administration can be neurotoxic to capsaicin-sensitive cells, especially in newborn animals. Active component of chili peppers.
Sigma Aldrich - 12084 external link
Biochem/physiol Actions
Prototype vanilloid receptor agonist. Neurotoxin; activates sensory neurons that give rise to unmyelinated C-fibers, many of which contain substance P. Topical application desensitizes the sensory nerve endings giving a paradoxical antinociceptive effect; systemic administration can be neurotoxic to capsaicin-sensitive cells, especially in newborn animals. Active component of chili peppers.
Toronto Research Chemicals - C175680 external link
A representative lot is a 5:1 E:Z mixture.Has been isolated from paprika and cayenne. It is used as a tool in neurobiological research. Prototype vanilloid receptor agonist. Topical analgesic.
Toronto Research Chemicals - C175685 external link
Capsaicin analogue (C175680). It is used as a tool in neurobiological research. Prototype vanilloid receptor agonist. Topical analgesic.

REFERENCES

REFERENCES

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