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17304

Sigma-Aldrich

Crocin

for microscopy

Synonym(s):

Crocetin digentiobiose ester

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About This Item

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

grade

for microscopy

Quality Level

100

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

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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.

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Bertha Montalvo-Hernández et al.
Journal of chromatography. A, 1236, 7-15 (2012-04-03)
Crocins are carotenoid derivates that have recently attracted the interest of the scientific community due to their nutraceutical properties. Saffron (dry Crocus sativus stigmas) is one of the main known sources of crocins. In this study the potential use of
Maryam Akbari-Fakhrabadi et al.
Journal of food biochemistry, 43(8), e12946-e12946 (2019-08-02)
We aimed to evaluate the effect of saffron (Crocus Sativus L.) treatment on endurance capacity, mitochondrial biogenesis, inflammation, antioxidant, and metabolic biomarkers in Wistar rats. Forty male rats were allocated equally into four groups: Saffron, Exercise and Saffron, Exercise and
R Fogelholm et al.
Journal of neurology, neurosurgery, and psychiatry, 55(12), 1121-1124 (1992-12-01)
Forty one (14.2%) of 288 patients with primary intracerebral haemorrhage occurring between September 1985 and December 1989 in Central Finland were on anticoagulant treatment at the onset of symptoms. In a sample of 29,000 subjects from the same population the
Amir Faramarzpour et al.
Veterinary research forum : an international quarterly journal, 10(3), 227-234 (2019-11-19)
Crocin, as a carotenoid compound of saffron, exerts a potent antioxidant property. Mesalazine is frequently used in the treatment of ulcerative colitis. This study investigated the effects of separated and combination treatments with crocin and mesalazine in a rat model
Mika Masaki et al.
Molecular nutrition & food research, 56(2), 304-308 (2011-11-01)
Crocus sativus L. (saffron) has been traditionally used for the treatment of insomnia and other diseases of the nervous systems. Two carotenoid pigments, crocin and crocetin, are the major components responsible for the various pharmacological activities of C. sativus L.
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