Hydrangeic acid

Hydrangeic acid
Names

Preferred IUPAC name 2-Hydroxy-6-[(E)-2-(4-hydroxyphenyl)ethen-1-yl]benzoic acid
Identifiers
CAS Number	491-79-2^N[PubChem]
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL248347
ChemSpider	4476740
PubChem CID	5318116
UNII	GYE4WJ5J43
InChI InChI=1S/C15H12O4/c16-12-8-5-10(6-9-12)4-7-11-2-1-3-13(17)14(11)15(18)19/h1-9,16-17H,(H,18,19)/b7-4+ Key: UWXXIBUTKVUHTR-QPJJXVBHSA-N InChI=1/C15H12O4/c16-12-8-5-10(6-9-12)4-7-11-2-1-3-13(17)14(11)15(18)19/h1-9,16-17H,(H,18,19)/b7-4+ Key: UWXXIBUTKVUHTR-QPJJXVBHBH
SMILES Oc2ccc(cc2)\C=C\c(c1C(O)=O)cccc1O
Properties
Chemical formula	C₁₅H₁₂O₄
Molar mass	256.257 g·mol⁻¹
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Chemical compound

Hydrangeic acid is a stilbenoid found in the leaves of Hydrangea macrophylla.^[1]

Hydrangeic acid is being investigated as a possible antidiabetic drug as it significantly lowered blood glucose, triglyceride and free fatty acid levels in laboratory animals.^[1]

References

^ ^a ^b Hydrangeic acid from the processed leaves of Hydrangea macrophylla var. thunbergii as a new type of anti-diabetic compound. Hailong Zhang, Hisashi Matsuda, Chihiro Yamashita, Seikou Nakamura and Masayuki Yoshikawa, European Journal of Pharmacology, Volume 606, Issues 1–3, 15 March 2009, Pages 255–261, doi:10.1016/j.ejphar.2009.01.005

Hydroxystilbenes and their glycosides (monomeric forms)

Dihydroxylated

Pinosylvin
3,4′-Dihydroxystilbene

Trihydroxylated

Resveratrol

Tetrahydroxylated

O-methylated

4-Methoxyresveratrol Gnetucleistol D (2-methoxyoxyresveratrol) Gnetucleistol E (3-methoxy-isorhapontigenin) Isorhapontigenin (3,4',5-trihydroxy-3'-methoxystilbene) Pinostilbene (3-methoxyresveratrol) Pterostilbene (3',5'-dimethoxyresveratrol) Rhapontigenin (piceatannol 4'-methyl ether)
Combretastatins	Combretastatin A-1 Combretastatin A-4

carboxylated

Hydrangeic acid

other acylations

3,5-Dihydroxy-4-isopropyl-trans-stilbene

Glycosides

Astringin (Piceatannol 3-O-glucoside)
Isorhapontin (Isorhapontigenin glucoside)
Mulberroside A (Oxyresveratrol diglucoside)

of resveratrol	Piceid (trans-Resveratrol-3-O-glucoside) trans-Resveratrol-3-O-glucuronide Resveratroloside (trans-resveratrol-4'-O-beta-D-glucopyranoside)
of rhapontigenin	Rhapontigenin 3-O-rutinoside 4'-Methoxy-(E)-resveratrol 3-O-rutinoside Rhaponticin (Rhapontigenin glucoside)