(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: 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

NAMES AND DATABASE IDS

Names

• 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

Database IDs

• CAS Number: 7553-53-9; 404-86-4
• EC Number: 206-969-8
• MDL Number: MFCD00017259
• Beilstein Number: 2816484
• PubChem SID: 162037753; 24853015; 24862158; 24847432; 24896598
• 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

• Acid pKa: 9.928692
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 3.749653
• LogD (pH = 7.4): 3.7483943
• Log P: 3.7496696
• Molar Refractivity: 90.3174 cm^3
• Polarizability: 34.670914 Å^3
• Polar Surface Area: 58.56 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: .0013 g/100 mL in water; Chloroform; DMSO; ethanol: soluble; H2O: insoluble; Methanol; soluble in alcohol, ether, benzene ; slightly soluble in CS₂. HCl, petroleum
• Apperance: Off-White to Pale Yellow Solid; pure dark red solid
• Melting Point: 60-62°C; 62 - 65°C; 62-65 °C; 62-65 °C(lit.); 62-65°C
• Boiling Point: 210 - 220°C (0.01 Torr); 210-212°C
• Flash Point: 113 °C; 235.4 °F
• Odor: highly volatile and pungent

Safety Information

• Storage Condition: -20°C; -20°C Freezer, Under Inert Atmosphere; 2-8°C
• RTECS: RA8530000
• European Hazard Symbols: Toxic (T)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 2; II
• Australian Hazchem: 2XE
• Risk Statements: 25-37/38-41-42/43; R:25; R24/25
• Safety Statements: 22-26-28-36/39-45; S:28-36/37/39-45-53; S26, S36/37/39, S45
• EU Classification: T2
• EU Hazard Identification Number: 6.1B
• Emergency Response Guidebook(ERG) Number: 154
• GHS Pictograms: GHS05; GHS06; GHS08
• GHS Signal Word: Danger
• Main Hazard: Toxic (T)
• NFPA704:
  

  1

  2

  0
• GHS Hazard statements: H301-H315-H317-H318-H334-H335
• GHS Precautionary statements: P261-P280-P301 + P310-P305 + P351 + P338-P342 + P311
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 2
• Storage Temperature: 2-8°C

Pharmacology Properties

• Target: vasopressin receptor
• Gene Information: human ... CYP1A2(1544), TRPV1(7442)rat ... Trpv1(83810), Trpv4(66026)
• Mechanism of Action: Gastric motility inhibitor; Prevents reaccumulation of substance-P in peripheral sensory neurons; Probable mechanism: substance-P-depletor

Product Information

• Purity: ~60%; >90%; ≥50% (HPLC); ≥95%; ≥99.0% (HPLC); 65-70%
• Grade: natural
• Salt Data: Free Base
• Compostion: capsaicin, 65%; dihydrocapsaicin, 35%
• Description: Isomers
• Impurities: ~35% dihydrocapsaicin
• Biological Source: from Capsicum sp.; Pungent principle of various Capsicum spp. (Solanaceae)
• Application(s): Irritant used for desensitisation of sensory neurones; Used as a counterirritant and topical analgesic for some skin conditions; Used as a selective probe for studying neurogenic inflammation and the role of nociceptors in human physiol
• Linear Formula: (CH3)2CHCH=CH(CH2)4CONHCH2C6H3-4-(OH)-3-(OCH3)

DETAILS

MP Biomedicals - 02199516

Synthetic (Natural compound obtained by total synthesis)
Assay(HPLC): >90%
Topical Analgesic(for neuralgia).

MP Biomedicals - 02190239

Purity: 65-70%
Contains up to 30-35% <->Dihydro analog
Induces substance P release from afferent nociceptive specific neurons.

Selleck Chemicals - S1990

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]

InterBioScreen - BB_NC-1023

Isomers

Sigma Aldrich - M2028

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 - M3403

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

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

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 - 21750

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.

Toronto Research Chemicals - C175685

Capsaicin analogue (C175680). It is used as a tool in neurobiological research. Prototype vanilloid receptor agonist. Topical analgesic.

Toronto Research Chemicals - C175680

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.

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