(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl 2,6,11,15-tetramethyl-16-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}methyl)heptadeca-2,4,6,8,10,12,14,16-octaenoate

• ChemBase编号: 155851
• 分子式: C46H68O23
• 平均质量: 989.01832
• 单一同位素质量: 988.41513844
• SMILES: C/C(=C\C=C\C=C(/C)\C=C\C=C(/C)\C(=O)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O)O)O)O)/C=C/C=C(\C)/C(=C)CO[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O)O)O)O
• Canonical SMILES: OC[C@H]1O[C@@H](OC[C@H]2O[C@@H](OCC(=C)/C(=C/C=C/C(=C/C=C/C=C(/C=C/C=C(/C(=O)O[C@@H]3O[C@H](CO[C@@H]4O[C@H](CO)[C@H]([C@@H]([C@H]4O)O)O)[C@H]([C@@H]([C@H]3O)O)O)\C)\C)/C)/C)[C@@H]([C@H]([C@@H]2O)O)O)[C@@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C46H68O23/c1-21(12-8-14-23(3)25(5)18-62-43-40(59)36(55)32(51)28(67-43)19-63-44-38(57)34(53)30(49)26(16-47)65-44)10-6-7-11-22(2)13-9-15-24(4)42(61)69-46-41(60)37(56)33(52)29(68-46)20-64-45-39(58)35(54)31(50)27(17-48)66-45/h6-15,26-41,43-60H,5,16-20H2,1-4H3/t26-,27-,28-,29-,30-,31-,32-,33-,34+,35+,36+,37+,38-,39-,40-,41-,43-,44-,45-,46+/m1/s1
• InChIKey: LUVDBMJRTUBHNX-ZTVQQPIHSA-N

名称和登记号

名称

• IUPAC标准名: (2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl 2,6,11,15-tetramethyl-16-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}methyl)heptadeca-2,4,6,8,10,12,14,16-octaenoate
• IUPAC传统名: (2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl 2,6,11,15-tetramethyl-16-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}methyl)heptadeca-2,4,6,8,10,12,14,16-octaenoate
• 别名: Crocetin digentiobiose ester; Crocin

登记号

• CAS号: 42553-65-1
• EC号: 255-881-6
• MDL号: MFCD00017495
• PubChem SID: 24850428; 162249989
• PubChem CID: 71312230

理论计算性质

• Acid pKa: 11.67302
• 质子受体: 22
• 质子供体: 14
• LogD (pH = 5.5): -3.0355606
• LogD (pH = 7.4): -3.0355835
• Log P: -3.0355604
• 摩尔折射率: 242.4525 cm^3
• 极化性: 95.353004 Å^3
• 极化表面积: 374.13 Å^2
• 可自由旋转的化学键: 21
• 里宾斯基五规则: false

分子性质

安全信息

• RTECS编号: HL7380000
• 德国WGK号: 3
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• 保存温度: 2-8°C

产品相关信息

• 级别: for microscopy
• Empirical Formula (Hill Notation): C44H64O24

详细说明

Sigma Aldrich - 17304

General description
A highly unsaturared diterpene dicarboxylic acid ester found in saffron.
Biochem/physiol Actions
Crocin alleviates some ethanol-induced impairments of learning and prevents ethanol-induced inhibition of hippocampal long-term potentiation (LTP), a form of activity-dependent synaptic plasticity that may underly learning and memory.1 Related CNS effects are specific to the digentiobiose ester; crocetin glucose gentiobiose ester is half as potent, and the diglucose ester has no effect at all.2
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. 17304.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.