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Curcumin-β-D-glucuronide

CAT: 0804-HY-138795-02Size: 5 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-138795-02Size:5 mg
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24/48H Stock Items & 2 to 6 Weeks non Stock Items.
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Description
Curcumin-β-D-glucuronide is a major metabolite after oral intake of Curcumin in hepatic tissue and portal blood. Curcumin-β-D-glucuronide can be used for the research of colon cancer[1][2].
CAS Number
227466-72-0
UNSPSC
12352005
Hazard Statement
H302+H312+H332, H315, H319, H335
Target
Endogenous Metabolite
Type
Reference compound
Related Pathways
Metabolic Enzyme/Protease
Applications
Cancer-programmed cell death
Field of Research
Cancer
Assay Protocol
https://www.medchemexpress.com/curcumin-β-d-glucuronide.html
Purity
98.01
Solubility
DMSO : 50 mg/mL (ultrasonic; warming; heat to 60°C)
Smiles
COC(C=C(C=C1)/C=C/C(CC(/C=C/C2=CC(OC)=C(C=C2)O)=O)=O)=C1O[C@@H]3O[C@@H]([C@H]([C@@H]([C@H]3O)O)O)C(O)=O
Molecular Formula
C27H28O12
Molecular Weight
544.50
Precautions
H302+H312+H332, H315, H319, H335
References & Citations
[1]Ozawa-Umeta H, et, al. Curcumin β-D-glucuronide exhibits anti-tumor effects on oxaliplatin-resistant colon cancer with less toxicity in vivo. Cancer Sci. 2020 May;111 (5) :1785-1793.|[2]Ozawa H, et, al. Curcumin β-D-Glucuronide Plays an Important Role to Keep High Levels of Free-Form Curcumin in the Blood. Biol Pharm Bull. 2017;40 (9) :1515-1524.
Shipping Conditions
Room Temperature
Storage Conditions
-20°C, 3 years; 4°C, 2 years (Powder)
Scientific Category
Reference compound1
Clinical Information
No Development Reported

Chemical Information

Curcumin glucuronide

Curcumin glucuronide is a diarylheptanoid.

CAS Number227466-72-0
PubChem CID71315012
IUPAC Name(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[4-[(1E,6E)-7-(4-hydroxy-3-methoxyphenyl)-3,5-dioxohepta-1,6-dienyl]-2-methoxyphenoxy]oxane-2-carboxylic acid
Molecular FormulaC27H28O12
Molecular Weight544.5
XLogP1.6
Topological Polar Surface Area189
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count12
Rotatable Bond Count11
Heavy Atom Count39
Formal Charge0
Complexity903
SMILES
COC1=C(C=CC(=C1)/C=C/C(=O)CC(=O)/C=C/C2=CC(=C(C=C2)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)C(=O)O)O)O)O)OC)O
InChI
InChI=1S/C27H28O12/c1-36-20-11-14(5-9-18(20)30)3-7-16(28)13-17(29)8-4-15-6-10-19(21(12-15)37-2)38-27-24(33)22(31)23(32)25(39-27)26(34)35/h3-12,22-25,27,30-33H,13H2,1-2H3,(H,34,35)/b7-3+,8-4+/t22-,23-,24+,25-,27+/m0/s1
InChIKey
BNSAVBGHRVFVNN-XSCLDSQRSA-N
Chemical Structure
2D Structure
2D structure of Curcumin glucuronide
CAS: 227466-72-0
CID: 71315012
Formula: C27H28O12
MW: 544.5
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight544.5
XLogP31.6
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count12
Rotatable Bond Count11
Exact Mass544.15807632
Monoisotopic Mass544.15807632
Topological Polar Surface Area189 Ų
Heavy Atom Count39
Formal Charge0
Complexity903
Isotope Atom Count0
Defined Atom Stereocenter Count5
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count2
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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