Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C21H21O11.Cl |
| Molecular Weight | 484.838 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 5 / 5 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[Cl-].OC[C@H]1O[C@@H](OC2=C([O+]=C3C=C(O)C=C(O)C3=C2)C4=CC=C(O)C(O)=C4)[C@H](O)[C@@H](O)[C@@H]1O
InChI
InChIKey=YTMNONATNXDQJF-UBNZBFALSA-N
InChI=1S/C21H20O11.ClH/c22-7-16-17(27)18(28)19(29)21(32-16)31-15-6-10-12(25)4-9(23)5-14(10)30-20(15)8-1-2-11(24)13(26)3-8;/h1-6,16-19,21-22,27-29H,7H2,(H3-,23,24,25,26);1H/t16-,17-,18+,19-,21-;/m1./s1
| Molecular Formula | C21H20O11 |
| Molecular Weight | 448.3769 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 5 / 5 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
| Molecular Formula | ClH |
| Molecular Weight | 36.461 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Cyanidin-3-glucoside suppresses B[a]PDE-induced cyclooxygenase-2 expression by directly inhibiting Fyn kinase activity. | 2011 Jul 15 |
|
| Malvidin-3-glucoside protects endothelial cells up-regulating endothelial NO synthase and inhibiting peroxynitrite-induced NF-kB activation. | 2012 Sep 30 |
|
| Effects of anthocyanins on the AhR-CYP1A1 signaling pathway in human hepatocytes and human cancer cell lines. | 2013 Jul 31 |
|
| Cyanidin-3-O-glucoside modulates intracellular redox status and prevents HIF-1 stabilization in endothelial cells in vitro exposed to chronic hypoxia. | 2014 Apr 21 |
|
| Palmitate-induced endothelial dysfunction is attenuated by cyanidin-3-O-glucoside through modulation of Nrf2/Bach1 and NF-κB pathways. | 2015 Dec 15 |
Patents
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 19:47:41 GMT 2023
by
admin
on
Fri Dec 15 19:47:41 GMT 2023
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| Record UNII |
8X15R84UEM
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| Record Status |
Validated (UNII)
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| Record Version |
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7084-24-4
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1151935
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C066411
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m3947
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230-384-7
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197081
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| Related Record | Type | Details | ||
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PARENT -> SALT/SOLVATE | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT |
This major anthocyanin was isolated by high-speed
countercurrent chromatography. HPLC-PDA, HPLC-MS/MS, and 1H NMR were used to confirm
the identity of this main anthocyanin of camu-camu.
Cyanidin-3-glucoside was identified as the major
pigment in the fruits from both regions, representing 89.5% in the fruits produced in Iguape and 88.0% in those from Mirandopolis.
Higher total anthocyanin content was detected in the fruits from Iguape (54.0
(25.9 mg/100 g) compared to those from Mirandopolis (30.3 (6.8 mg/100 g), most likely because of the lower temperatures in the Iguape region.
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