(6E)-N-[(4-hydroxy-3-methoxyphenyl)methyl]-8-methylnon-6-enamide

• ChemBase编号: 72832
• 分子式: C18H27NO3
• 平均质量: 305.41188
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: (6E)-N-[(4-hydroxy-3-methoxyphenyl)methyl]-8-methylnon-6-enamide; N-[(4-hydroxy-3-methoxyphenyl)methyl]-8-methylnon-6-enamide
• IUPAC传统名: capsaicin; N-[(4-hydroxy-3-methoxyphenyl)methyl]-8-methylnon-6-enamide; (6E)-N-[(4-hydroxy-3-methoxyphenyl)methyl]-8-methylnon-6-enamide
• 别名: 8-甲基-N-香草基-反-6-壬烯酰胺; 辣椒碱; 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

登记号

• CAS号: 7553-53-9; 404-86-4
• EC号: 206-969-8
• MDL号: MFCD00017259
• Beilstein号: 2816484
• PubChem SID: 162037753; 24853015; 24862158; 24847432; 24896598
• PubChem CID: 1548943
• CHEBI ID: 3374
• ATC码: N01BX04; M02AB01
• CHEMBL: 294199
• Chemspider ID: 1265957
• KEGG ID: C06866
• 美国药典/FDA物质标识码: S07O44R1ZM
• 维基百科标题: Capsaicin

理论计算性质

• Acid pKa: 9.928692
• 质子受体: 3
• 质子供体: 2
• LogD (pH = 5.5): 3.749653
• LogD (pH = 7.4): 3.7483943
• Log P: 3.7496696
• 摩尔折射率: 90.3174 cm^3
• 极化性: 34.670914 Å^3
• 极化表面积: 58.56 Å^2
• 可自由旋转的化学键: 9
• 里宾斯基五规则: true

分子性质

理化性质

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

安全信息

• 保存条件: -20°C; -20°C Freezer, Under Inert Atmosphere; 2-8°C
• RTECS编号: RA8530000
• 欧盟危险性物质标志: 有毒(Toxic) (T)
• 联合国危险货物编号: 2811
• 德国WGK号: 3
• 联合国危险货物等级: 6.1
• 联合国危险货物包装类别(PG): 2; II
• 澳大利亚Hazchem: 2XE
• 危险公开号: 25-37/38-41-42/43; R:25; R24/25
• 安全公开号: 22-26-28-36/39-45; S:28-36/37/39-45-53; S26, S36/37/39, S45
• 欧盟危险货物分类: T2
• 欧盟危险识别号(EUHIN): 6.1B
• 美国ERG指导号: 154
• GHS危险品标识: GHS05; GHS06; GHS08
• GHS警示词: Danger
• 主要危害: Toxic (T)
• NFPA704:
  

  1

  2

  0
• GHS危险声明: H301-H315-H317-H318-H334-H335
• GHS警示性声明: P261-P280-P301 + P310-P305 + P351 + P338-P342 + P311
• 个人保护装置: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 2
• 保存温度: 2-8°C

药理学性质

• 作用靶点: vasopressin receptor
• 相关基因信息: human ... CYP1A2(1544), TRPV1(7442)rat ... Trpv1(83810), Trpv4(66026)
• 生物活性机理: Gastric motility inhibitor; Prevents reaccumulation of substance-P in peripheral sensory neurons; Probable mechanism: substance-P-depletor

产品相关信息

• 纯度: ~60%; >90%; ≥50% (HPLC); ≥95%; ≥99.0% (HPLC); 65-70%
• 级别: natural
• 成盐信息: Free Base
• 主要成分: capsaicin, 65%; dihydrocapsaicin, 35%
• 简要说明: Isomers
• 杂质: ~35% dihydrocapsaicin
• 生物来源: from Capsicum sp.; Pungent principle of various Capsicum spp. (Solanaceae)
• 应用领域: 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
• 线性分子式: (CH3)2CHCH=CH(CH2)4CONHCH2C6H3-4-(OH)-3-(OCH3)

详细说明

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

包装
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

包装
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.

参考文献

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