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Details

Stereochemistry ABSOLUTE
Molecular Formula C38H54O19
Molecular Weight 814.824
Optical Activity UNSPECIFIED
Defined Stereocenters 15 / 15
E/Z Centers 7
Charge 0

SHOW SMILES / InChI
Structure of CROCETIN GENTIOBIOSYLGLUCOSYL ESTER

SMILES

CC(\C=C\C=C(/C)C(=O)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)=C/C=C/C=C(C)/C=C/C=C(\C)C(=O)O[C@@H]2O[C@H](CO[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@@H](O)[C@H](O)[C@H]2O

InChI

InChIKey=CZSBHMFVVLYIQQ-DRVLGOCHSA-N
InChI=1S/C38H54O19/c1-18(11-7-13-20(3)34(50)56-37-32(48)29(45)26(42)23(16-40)54-37)9-5-6-10-19(2)12-8-14-21(4)35(51)57-38-33(49)30(46)27(43)24(55-38)17-52-36-31(47)28(44)25(41)22(15-39)53-36/h5-14,22-33,36-49H,15-17H2,1-4H3/b6-5+,11-7+,12-8+,18-9+,19-10+,20-13+,21-14+/t22-,23-,24-,25-,26-,27-,28+,29+,30+,31-,32-,33-,36-,37+,38+/m1/s1

HIDE SMILES / InChI

Molecular Formula C38H54O19
Molecular Weight 814.824
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 15 / 15
E/Z Centers 7
Optical Activity UNSPECIFIED

Crocetin gentiobiosylglucosyl ester (Crocin II) is extracted from saffron (Crocus sativus L.). Tricrocin is a water soluble crocetin glycoside, a carotenoid pigment of saffron (Crocus sativus L.) that has been used as a spice for flavoring and coloring food preparations, and in Chinese traditional medicine as an anodyne or tranquilizer. Saffron is now used worldwide in folk medicine and is reputed to be useful in treating various human disorders such as heart and blood disorders. Stroke and heart attack are involved in reputed folkloric uses of saffron. Saffron is orally administrated as a decoction. Saffron extract exerts a protective effect on renal ischemia reperfusion induced oxidative damage in rats; Crocetin esters present in saffron stigmas and in Gardenia jasminoides Ellis fruit are the compounds responsible for their color. Crocin, in general term, includes Crocin-I (Crocetin-di-beta -D-gentiobiosyl ester), Crocin-II (Crocetin-beta-D-gentiobiosyl-beta-D-glucosyl ester), Crocin-III (Crocetin-mono-beta-D-gentiobiosyl ester), Crocin-IV (beta-D-monoglucoside ester of monomethyl alpha-crocetin). Saffron from Zhejiang (containing 21.15 ug/ml of Crocetin gentiobiosylglucosyl ester) has significant antitumor effects in vitro and in vivo through caspase-8-caspase-9-caspase-3 mediated cell apoptosis. It thus appears to have a potential as a therapeutic agent.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: Concentration of Crocetin gentiobiosylglucosyl ester (Crocin II) in Jiande Saffron Extract is 21.15 ug/ml.
Mice: In vivo, when mice were orally administered Jiande saffron extract at dose of 100mg/kg/d for 28 days, xenograft tumor size was reduced.
Route of Administration: Oral
In Vitro Use Guide
Curator's Comment: Concentration of Crocetin gentiobiosylglucosyl ester (Crocin II) in Jiande Saffron Extract is 21.15 ug/ml.
Jiande Saffron Extract inhibited A549 cells growth with IC50 value of 1.03 mg/ml.
Substance Class Chemical
Created
by admin
on Sat Dec 16 10:00:59 GMT 2023
Edited
by admin
on Sat Dec 16 10:00:59 GMT 2023
Record UNII
ZF2MOD2N6Y
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CROCETIN GENTIOBIOSYLGLUCOSYL ESTER
Common Name English
.BETA.-D-GLUCOPYRANOSE, 6-O-.BETA.-D-GLUCOPYRANOSYL-, 1-((2E,4E,6E,8E,10E,12E,14E)-.BETA.-D-GLUCOPYRANOSYL 2,6,11,15-TETRAMETHYL-2,4,6,8,10,12,14-HEXADECAHEPTAENEDIOATE)
Systematic Name English
TRANS-CROCETIN (.BETA.-D-GLUCOSYL)-(.BETA.-D-GENTIOBIOSYL) ESTER
Common Name English
ALL-TRANS-CROCETIN .BETA.-D-GENTIOBIOSYL-.BETA.-D-GLUCOSYL ESTER
Common Name English
Code System Code Type Description
EPA CompTox
DTXSID80856143
Created by admin on Sat Dec 16 10:00:59 GMT 2023 , Edited by admin on Sat Dec 16 10:00:59 GMT 2023
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FDA UNII
ZF2MOD2N6Y
Created by admin on Sat Dec 16 10:00:59 GMT 2023 , Edited by admin on Sat Dec 16 10:00:59 GMT 2023
PRIMARY
PUBCHEM
9940690
Created by admin on Sat Dec 16 10:00:59 GMT 2023 , Edited by admin on Sat Dec 16 10:00:59 GMT 2023
PRIMARY
CAS
55750-84-0
Created by admin on Sat Dec 16 10:00:59 GMT 2023 , Edited by admin on Sat Dec 16 10:00:59 GMT 2023
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