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Merck

17304

Crocin

suitable for microscopy

Sinónimos:

Crocetin digentiobiose ester

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Acerca de este artículo

Fórmula empírica (notación de Hill):
C44H64O24
Número CAS:
Peso molecular:
976.96
NACRES:
NA.47
PubChem Substance ID:
UNSPSC Code:
12352200
EC Number:
255-881-6
MDL number:
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InChI key

LUVDBMJRTUBHNX-RSXXRLSLSA-N

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

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

form

solid

suitability

suitable for microscopy

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

storage temp.

2-8°C

Quality Level

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General description

A highly unsaturared diterpene dicarboxylic acid ester found in saffron.
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.

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.

Clase de almacenamiento

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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Zahoor Ahmed Wani et al.
Scientific reports, 7(1), 8598-8598 (2017-08-19)
Crocus sativus is the only plant species which produces apocarotenoids like crocin, picrocrocin and safranal in significant amounts. These compounds impart organoleptic properties to saffron (dried stigmas of Crocus flower) making it world's costliest spice. Crocus apocarotenoids have tremendous medicinal
S C Marić et al.
The Journal of biological chemistry, 267(26), 18915-18923 (1992-09-15)
Genomic clones for the S-adenosylmethionine (AdoMet) decarboxylase gene were isolated from a human chromosome 6 DNA library. In addition, polymerase chain reaction and specific primers were used to amplify fragments from chromosomal DNA covering exonic regions not found in the
Mona A Hussain et al.
Oxidative medicine and cellular longevity, 2021, 8841726-8841726 (2021-02-26)
Doxorubicin is a drug that belongs to the anthracycline antibiotics. Nephrotoxicity is one of the serious side effects of doxorubicin treatment. Crocin, which is one of the most bioactive components of saffron, has antioxidant, anti-inflammatory, and antitumor effects. The current
Sutong Li et al.
Cellular physiology and biochemistry : international journal of experimental cellular physiology, biochemistry, and pharmacology, 42(4), 1481-1492 (2017-07-19)
Diabetic nephropathy (DN) is a microangiopathic disease characterized by excessive urinary albumin excretion, which occurs in 30% of patients with diabetes mellitus. It is the second leading cause of end-stage renal diseases in China. Nuclear factor-kappa B (NF-κB) is reported
R S Namba et al.
The Journal of hand surgery, 17(6), 1148-1153 (1992-11-01)
Early care after surgery or trauma to the extremities often includes a period of immobilization. The resultant joint stiffness may require extensive rehabilitation and may permanently limit function of the limb. Posttraumatic joint stiffness is particularly vexing in the small

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