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
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