Gambogic acid

Gambogic acid
Names
Preferred IUPAC name
(2Z)-4-[(1R,3aS,5S,11R,14aS)-8-Hydroxy-3,3,11-trimethyl-13-(3-methylbut-2-en-1-yl)-11-(4-methylpent-3-en-1-yl)-7,15-dioxo-3a,4,5,7-tetrahydro-1H,3H,11H-1,5-methanofuro[3,4-g]pyrano[3,2-b]xanthen-1-yl]-2-methylbut-2-enoic acid
Other names
β-Guttiferin
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.159.336 Edit this at Wikidata
UNII
  • InChI=1S/C38H44O8/c1-20(2)10-9-15-36(8)16-14-24-29(39)28-30(40)26-18-23-19-27-35(6,7)46-37(33(23)41,17-13-22(5)34(42)43)38(26,27)45-32(28)25(31(24)44-36)12-11-21(3)4/h10-11,13-14,16,18,23,27,39H,9,12,15,17,19H2,1-8H3,(H,42,43)/b22-13-/t23-,27+,36-,37+,38-/m1/s1 ☒N
    Key: GEZHEQNLKAOMCA-RRZNCOCZSA-N ☒N
  • InChI=1/C38H44O8/c1-20(2)10-9-15-36(8)16-14-24-29(39)28-30(40)26-18-23-19-27-35(6,7)46-37(33(23)41,17-13-22(5)34(42)43)38(26,27)45-32(28)25(31(24)44-36)12-11-21(3)4/h10-11,13-14,16,18,23,27,39H,9,12,15,17,19H2,1-8H3,(H,42,43)/b22-13-/t23-,27+,36-,37+,38-/m1/s1
    Key: GEZHEQNLKAOMCA-RRZNCOCZBX
  • O=C1/C4=C/[C@H]6C(=O)[C@@]5(OC([C@@H]([C@]45Oc3c1c(O)c2\C=C/[C@@](Oc2c3C\C=C(/C)C)(C)CC\C=C(/C)C)C6)(C)C)C/C=C(\C(=O)O)C
Properties
C38H44O8
Molar mass 628.762 g·mol−1
Appearance Amorphous orange solid
Density 1.29 g/cm3
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Gambogic acid is a xanthonoid that is derived from the brownish or orange resin from Garcinia hanburyi. Garcinia hanburyi is a small to medium-sized evergreen tree (up to approximately 15 m in height) with smooth grey bark. It is native to Cambodia, southern Vietnam, and Thailand and has been successfully introduced in Singapore.[1][2]

  1. ^ "Garcinia hanburyi Hook" (PDF). World Agroforestry Center.
  2. ^ "Garcinia hanburyi Hook". AgroForestry Tree Database. World Agroforestry Center.