(2E)-4-[(2S,17S)-12-Hydroxy-8,21,21-trimethyl-5-(3-methyl-2-buten-1-yl)-8-(4-methyl-3-penten-1-yl)-14,18-dioxo-3,7,20-trioxahexacyclo[15.4.1.0~2,15~.0~2,19~.0~4,13~.0~6,11~]docosa-4(13),5,9,11,15-pent aen-19-yl]-2-methyl-2-butenoic acid

Basic Information

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CAS Number

2752-65-0

Molecular Formula

C38H44O8

Molecular Weight

628.76 g/mol

Chemical Classification

Basic Chemical Raw Materials Organic Chemicals Carboxylic Acids

Basic Chemical Raw Materials Organic Chemicals Ketones

Basic Chemical Raw Materials Organic Chemicals Ethers

Basic Chemical Raw Materials Organic Chemicals Heterocyclic Compounds

Pharmaceutical Chemicals Pharmaceutical Intermediates Heterocyclic Intermediates

Fine Chemicals Dyes and Pigments Organic Dyes

Fine Chemicals Surfactants Anionic Surfactants

Laboratory Chemicals Research Chemicals Biochemical Reagents

Basic Physical Properties

Physical State

yellow to orange

Melting Point

88.5°C

Boiling Point

586.06°C (rough estimate)

Density

1.1057 (rough estimate)

Flash Point

251.4±27.8 °C

Solubility

DMSO: ≥10mg/mL

Refractive Index

1.5290 (estimate)

Specific Rotation

D20 -685° (methanol)

SMILES

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CC(=CCCC1(C=CC2=C(C3=C(C(=C2O1)CC=C(C)C)OC45C6CC(C=C4C3=O)C(=O)C5(OC6(C)C)CC=C(C)C(=O)O)O)C)C

InChI

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

InChIKey

GEZHEQNLKAOMCA-LVKRKGINSA-N

LogP

7.23930000000001

pKa

4.58±0.36(Predicted)

Topological Polar Surface Area

119.36000000000001 Å²

Hydrogen Bond Donor/Acceptor

2 / 8

Complexity

1490

Safety Information

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GHS Hazard Pictograms

H301

H315

H319

H335

Hazard Statement

H301 Toxic if swallowed
Acute toxicity, oral

H315 Causes skin irritation
Skin corrosion/irritation

H319 Causes serious eye irritation
Serious eye damage/eye irritation

H335 May cause respiratory irritation
Specific target organ toxicity, single exposure; Respiratory tract irritation

Storage Conditions

-20℃

Toxicity

LD50 unreported in mammal (species unspecified): 55mg/kg

Synonyms & References

English

AKOS024463359
BP-22199
CHEBI:67521
CHEMBL555017
(-)-Gambogic Acid
DTXSID101029723
CS-1456
(Z)-4-[(1S,2S,8R,17S,19R)-12-hydroxy-8,21,21-trimethyl-5-(3-methylbut-2-enyl)-8-(4-methylpent-3-enyl)-14,18-dioxo-3,7,20-trioxahexacyclo[15.4.1.02,15.02,19.04,13.06,11]docosa-4(13),5,9,11,15-pentaen-19-yl]-2-methylbut-2-enoic acid
H10129
Gambogic acid, >=95% (HPLC), powder
R-gambogic acid
MFCD16878985
Guttatic acid
(Z)-4-((1S,3aR,5S,11R,14aS)-8-hydroxy-2,2,11-trimethyl-13-(3-methylbut-2-en-1-yl)-11-(4-methylpent-3-en-1-yl)-4,7-dioxo-1,2,5,7-tetrahydro-11H-1,5-methanofuro[3,2-g]pyrano[3,2-b]xanthen-3a(4H)-yl)-2-methylbut-2-enoic acid
UNII-8N585K83U2
A-Guttilactone
Cambogic acid
s2448
GAMBOGICACID
A-Guttiferin
CCG-270284
beta-Guttiferin
SCHEMBL16160279
GEZHEQNLKAOMCA-RRZNCOCZSA-N
Q5519727
AC-34804
2-BUTENOIC ACID, 2-METHYL-4-((1R,3AS,5S,11R,14AS)-3A,4,5,7-TETRAHYDRO-8-HYDROXY-3,3,11-TRIMETHYL-13-(3-METHYL-2-BUTEN-1-YL)-11-(4-METHYL-3-PENTEN-1-YL)-7,15-DIOXO-1,5-METHANO-1H,3H,11H-FURO(3,4-G)PYRANO(3,2-B)XANTHEN-1-YL)-, (2Z)-
alpha-Gambogic acid
Gambogic-acid
.beta.-Guttiferin