Structure Database (LMSD)
Common Name
Crocetin
Systematic Name
8,8'-Diapocarotene-8,8'-dioic acid
Synonyms
3D model of Crocetin
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Category
Main Class
Sub Class
Level 4 Class
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
Plant Cell, 2003
Pubmed ID:
12509521
DOI:
10.1105/tpc.006536
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
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
Admin
Created at
-
Updated at
9th Dec 2020