Structure Database (LMSD)

Common Name
Crocetin
Systematic Name
8,8'-Diapocarotene-8,8'-dioic acid
Synonyms
LM ID
LMPR0104010020
Formula
Exact Mass
Calculate m/z
328.16746
Status
Curated


Classification

Biological Context

Transcrocetin is a natural apocarotenoid isolated from C. sativus and G. jasminoides that has antioxidant, antiproliferative, anti-inflammatory, cardioprotective, and antinociceptive properties.1,2,3,4,5,6 It scavenges 2,2-diphenyl-1-picrylhydrazyl (DPPH) radicals (IC50 = 17.8 μg/ml) and inhibits growth of MKN28 stomach, MCF-7 breast, and Caco-2 colon cancer cell lines (IC50s = 53, 63, and 103 μM, respectively).2,3 Transcrocetin (20 μM) protects primary rat microglial cells from LPS-induced death and decreases LPS-induced production of intracellular reactive oxygen species (ROS), TNF-α, IL-1β, and NF-κB.4 Transcrocetin (100 mg/kg) increases the level of glutathione (GSH), catalase (CAT), creatine kinase (CK), and lactate dehydrogenase (LDH) in cardiac tissue in a rat model of myocardial infarction induced by isoproterenol .5 It also increases the pressure threshold and latency to withdrawal in response to mechanical and thermal stimuli, respectively, indicating a decrease in allodynia in a mouse model of spared nerve injury when administered intrathecally at a dose of 30 mg/kg.6

This information has been provided by Cayman Chemical

References

2. Zhang, W., Li, Y., and Ge, Z. Cardiaprotective effect of crocetin by attenuating apoptosis in isoproterenol induced myocardial infarction rat model. Biomed. Pharmacother. 93, 376-382 (2017).
6. Pfister, S.L., Meyer, P., Steck, A., et al. Isolation and structure elucidation of carotenoid−glycosyl esters in gardenia fruits (Gardenia jasminoides Ellis) and saffron (Crocus sativus Linne). J. Agric. Food Chem. 44(9), 2612-2615 (1996).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Crocus sativus (#82528)
Magnoliopsida (#3398)
Oxidative remodeling of chromoplast carotenoids: identification of the carotenoid dioxygenase CsCCD and CsZCD genes involved in Crocus secondary metabolite biogenesis.,
Plant Cell, 2003
Pubmed ID: 12509521

String Representations

InChiKey (Click to copy)
PANKHBYNKQNAHN-MQQNZMFNSA-N
InChi (Click to copy)
InChI=1S/C20H24O4/c1-15(11-7-13-17(3)19(21)22)9-5-6-10-16(2)12-8-14-18(4)20(23)24/h5-14H,1-4H3,(H,21,22)(H,23,24)/b6-5+,11-7+,12-8+,15-9+,16-10+,17-13+,18-14+
SMILES (Click to copy)
C(O)(=O)/C(/C)=C/C=C/C(/C)=C/C=C/C=C(\C)/C=C/C=C(\C)/C(O)=O

Other Databases

Wikipedia
KEGG ID
CHEBI ID
LIPIDBANK ID
VCA1141
PubChem CID
Cayman ID

Calculated Physicochemical Properties

Heavy Atoms 24
Rings 0
Aromatic Rings 0
Rotatable Bonds 8
Van der Waals Molecular Volume 365.96
Topological Polar Surface Area 74.60
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 4
logP 4.61
Molar Refractivity 97.72

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Created at
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Updated at
9th Dec 2020