17304

Crocin

for microscopy

• Synonym(s): Crocetin digentiobiose ester
• Empirical Formula (Hill Notation): C₄₄H₆₄O₂₄
• CAS Number: 42553-65-1
• Molecular Weight: 976.96
• EC Number: 255-881-6
• MDL number: MFCD00017495
• UNSPSC Code: 12352200
• PubChem Substance ID: 57647630
• NACRES: NA.47

Properties

• grade: for microscopy
• form: solid
• application(s): metabolomics; vitamins, nutraceuticals, and natural products
• storage temp.: 2-8°C
• SMILES string: CC(=C\C=C\C=C(C)\C=C\C=C(/C)C(=O)O[C@@H]1O[C@H](CO[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@@H](O)[C@H](O)[C@H]1O)\C=C\C=C(\C)C(=C)CO[C@@H]3O[C@H](CO[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)[C@@H](O)[C@H](O)[C@H]3O
• 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/b7-6+,12-8+,13-9+,21-10-,22-11+,23-14-,24-15+/t26-,27-,28-,29-,30-,31-,32-,33-,34+,35+,36+,37+,38-,39-,40-,41-,43-,44-,45-,46+/m1/s1
• InChI key: LUVDBMJRTUBHNX-RSXXRLSLSA-N

Description

General description

Crocin (CR) is a water-soluble carotenoid found in Gardenia jasmi-noides Ellis and Crocus sativus (saffron). It has two D-gentiobioside glycosyl esters in its structure. CR is one of the major bioactive compounds of saffron contributing to its red color.

A highly unsaturared diterpene dicarboxylic acid ester found in saffron.

Application

Crocin has been used:

• as a reference standard to detect its presence in Crocus sativus L. extract using high-performance liquid chromatography technique
• to investigate its protective effects as an antioxidant and anti-inflammatory agent against doxorubicin-induced nephrotoxicity in rats
• to test antitumor effects and its role in promoting autophagy and apoptosis and inhibiting the progression of cervical cancer on SiHa cells and female BALB/c nude mice
• as a co-treatment with cisplatin to test its protective effect against cisplatin (CIS)-induced testicular toxicity in rats

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. 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.

Crocin exerts antioxidant, anti-inflammation, anti-cancer, antidegenerative, and antidiabetic properties.

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)