Curcumin beta-D-Glucuronide
Curcumin beta-D-Glucuronide is a Phase II metabolic conjugate formed via glucuronic acid linkage to a phenolic hydroxyl group of curcumin, featuring a beta-D-anomeric configuration at the glycosidic bond. The compound retains the bis-phenolic core of curcumin with an additional uronic acid moiety, introducing a carboxylic acid and multiple hydroxyl functionalities. This conjugation enhances water solubility relative to the parent compound, facilitating excretion. It serves as an HPLC reference standard for quantifying glucuronidation-derived impurities in curcumin-based pharmaceuticals.
On Request
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
📝 Synonyms
Curcumin glucuronide
227466-72-0
Curcumin beta-D-glucuronide
BE1PK7RL4M
Curcumin beta-O-glucuronide
(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
DTXSID20747384
(2S,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-(4-((1E,4Z,6E)-5-hydroxy-7-(4-hydroxy-3-methoxyphenyl)-3-oxohepta-1,4,6-trien-1-yl)-2-methoxyphenoxy)tetrahydro-2H-pyran-2-carboxylic acid
(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
4-((1E,6E)-7-(4-Hydroxy-3-methoxyphenyl)-3,5-dioxo-1,6-heptadien-1-yl)-2-methoxyphenyl beta-D-glucopyranosiduronic acid
🔬 Chemical Identifiers
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=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
BNSAVBGHRVFVNN-XSCLDSQRSA-N
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