(5S)-5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)decan-3-one

• ChemBase编号: 127560
• 分子式: C17H26O4
• 平均质量: 294.38594
• 单一同位素质量: 294.18310931
• SMILES: O=C(C[C@@H](O)CCCCC)CCc1cc(OC)c(O)cc1
• Canonical SMILES: CCCCC[C@@H](CC(=O)CCc1ccc(c(c1)OC)O)O
• InChI: InChI=1S/C17H26O4/c1-3-4-5-6-14(18)12-15(19)9-7-13-8-10-16(20)17(11-13)21-2/h8,10-11,14,18,20H,3-7,9,12H2,1-2H3/t14-/m0/s1
• InChIKey: NLDDIKRKFXEWBK-AWEZNQCLSA-N

名称和登记号

名称

• IUPAC标准名: (5S)-5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)decan-3-one
• IUPAC传统名: gingerol
• 别名: 5-羟基-1-(4-羟基-3-甲氧基苯基)-3-癸酮; 6-姜辣醇; 姜辣素; 6-姜酚; 3-Decanone, 5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-, (5S)-; 5-Hydroxy-1-(4-hydroxy-3-methoxyphenyl)-3-decanone; 6-Gingerol; [6]-Gingerol; (+)-5-Hydroxy-1-(4-hydroxy-3-methoxyphenyl)-3-decanone; (5S)-[6]-Gingerol; (S)-(+)-[6]Gingerol; (S)-[6]Gingerol; [6]-Gingerol; (+)-[6]-Gingerol; (5S)-5-Hydroxy-1-(4-hydroxy-3-methoxyphenyl)-3-decanone; (S)-(+)-5-Hydroxy-1-(4-hydroxy-3-methoxyphenyl)-3-decanone; Gingerol

登记号

• CAS号: 23513-14-6
• MDL号: MFCD00210507
• PubChem SID: 162221879
• PubChem CID: 442793
• CHEMBL: 402978
• Chemspider ID: 391126
• KEGG ID: C10462
• 美国药典/FDA物质标识码: 925QK2Z900
• 维基百科标题: Gingerol

理论计算性质

• Acid pKa: 9.945873
• 质子受体: 4
• 质子供体: 2
• LogD (pH = 5.5): 3.6165044
• LogD (pH = 7.4): 3.615294
• Log P: 3.61652
• 摩尔折射率: 83.1092 cm^3
• 极化性: 32.557247 Å^3
• 极化表面积: 66.76 Å^2
• 可自由旋转的化学键: 10
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: methanol: soluble1 mg/mL, clear, colorless
• 熔点: 30-32 °C

安全信息

• 保存条件: protect from light; under inert gas
• RTECS编号: HE0757000
• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 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): 3
• 危险公开号: 22-36/37/38
• 安全公开号: 26-36/37
• GHS危险品标识: GHS06
• GHS警示词: Danger
• GHS危险声明: H301-H315-H319-H335
• GHS警示性声明: P261-P301 + P310-P305 + P351 + P338
• 个人保护装置: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• RID/ADR: UN 2811 6.1/PG 3
• 保存温度: -20°C; 2-8°C

产品相关信息

• 纯度: ≥95.0% (HPLC); ≥98% (HPLC)
• 级别: analytical standard
• 有效期: (expiry date on the label)
• 运输包装: dry ice
• Empirical Formula (Hill Notation): C17H26O4

详细说明

Sigma Aldrich - G1046

Biochem/physiol Actions
存在于生姜 (Zingiber officinale) 中的具有抗氧化活性的生物活性化合物，1可用作抗炎剂和抗肿瘤剂。6-姜酚通过巨噬细胞下调促炎细胞因子的释放。2已证明它可通过阻断经佛波酯刺激的小鼠皮肤中 p38 MAP 激酶和 NF-κB 的活化来抑制 COX-2 的表达。3
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. G1046.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Sigma Aldrich - 50866

Biochem/physiol Actions
存在于生姜 (Zingiber officinale) 中的具有抗氧化活性的生物活性化合物，1可用作抗炎剂和抗肿瘤剂。6-姜酚通过巨噬细胞下调促炎细胞因子的释放。2已证明它可通过阻断经佛波酯刺激的小鼠皮肤中 p38 MAP 激酶和 NF-κB 的活化来抑制 COX-2 的表达。3

Toronto Research Chemicals - G387205

(+)-[6]-Gingerol is a bioactive compound found in ginger (Zingiber officinale) with antioxidant activity, which functions as an anti-inflammatory and antitumor agent. (+)-[6]-Gingerol down regulates proinflammatory cytokine release by macrophages. (+)-[6]

参考文献

• Aeschbach, R. et al.: Food Chem. Toxicol., 32, 31 (1994)
• Tripathi, S. et al.: J. Surg. Res., 130, 318 (1994)
• Kim, S.O., et al.: Oncogene 24, 2558 (1994)