(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 ID: 155851
• Molecular Formular: C46H68O23
• Molecular Mass: 989.01832
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: (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 Traditional name: (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
• Synonyms: Crocetin digentiobiose ester; Crocin

Database IDs

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

CALCULATED PROPERTIES

• Acid pKa: 11.67302
• H Acceptors: 22
• H Donor: 14
• LogD (pH = 5.5): -3.0355606
• LogD (pH = 7.4): -3.0355835
• Log P: -3.0355604
• Molar Refractivity: 242.4525 cm^3
• Polarizability: 95.353004 Å^3
• Polar Surface Area: 374.13 Å^2
• Rotatable Bonds: 21
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• RTECS: HL7380000
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

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

DETAILS

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.