Skip Navigation
ChemIDplus A TOXNET DATABASE LiteBrowseAdvanced

Substance Name: Gossypol
RN: 303-45-7
UNII: KAV15B369O
InChIKey: QBKSWRVVCFFDOT-UHFFFAOYSA-N

Note

  • A dimeric sesquiterpene found in cottonseed (GOSSYPIUM). The (-) isomer is active as a male contraceptive (CONTRACEPTIVE AGENTS, MALE) whereas toxic symptoms are associated with the (+) isomer.

Molecular Formula

  • C30-H30-O8

Molecular Weight

  • 518.559
 

Classification Codes

  • Contraceptive Agents
  • Contraceptive Agents, Male
  • Human Data
  • Mutation Data
  • Natural Product
  • Reproductive Control Agents
  • Reproductive Effect
* denotes mobile formatted website

Links to Resources


Search for this InChIKey on the Web

Names and Synonyms

Name of Substance

  • Gossypol

MeSH Heading

  • Gossypol

Synonyms

  • 2,2'-Bis(1,6,7-trihydroxy-3-methyl-5-isopropyl-8-aldehydonaphthalene)
  • 4-08-00-03754 (Beilstein Handbook Reference)
  • 8-Formyl-1,6,7-trihydroxy-5-isopropyl-3-methyl-2,2'-bisnaphthalene
  • AI3-22957
  • BL 193
  • BRN 1917878
  • CCRIS 2689
  • Gossypol
  • HSDB 7872
  • No Fertil
  • NSC 56817
  • NSC 624336
  • Pogosin
  • Tash 1
  • UNII-KAV15B369O

Systematic Names

  • (2,2'-Binaphthalene)-8,8'-dicarboxaldehyde, 1,1',6,6',7,7'-hexahyd
  • (2,2'-Binaphthalene)-8,8'-dicarboxaldehyde, 1,1',6,6',7,7'-hexahydroxy-3,3'-dimethyl-5,5'-bis(1-methylethyl)-
  • (2,2'-Binaphthalene)-8,8'-dicarboxaldehyde, 1,1',6,6',7,7'-hexahydroxy-5,5'-diisopropyl-3,3'-dimethyl-
  • Gossypol

Registry Numbers

CAS Registry Number

  • 303-45-7

FDA UNII

  • KAV15B369O

Other Registry Numbers

  • 40112-23-0
  • 732279-01-5

System Generated Number

  • 0000303457

Structure Descriptors

InChI

1S/C30H30O8/c1-11(2)19-15-7-13(5)21(27(35)23(15)17(9-31)25(33)29(19)37)22-14(6)8-16-20(12(3)4)30(38)26(34)18(10-32)24(16)28(22)36/h7-12,33-38H,1-6H3

InChIKey

QBKSWRVVCFFDOT-UHFFFAOYSA-N

Smiles

c1(c(c2c(cc1C)c(c(c(c2C=O)O)O)C(C)C)O)c1c(c2c(c(c(c(c2C=O)O)O)C(C)C)cc1C)O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
pig LD50 oral 550mg/kg (550mg/kg) BEHAVIORAL: MUSCLE WEAKNESS

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
Journal of the American Oil Chemists' Society. Vol. 40, Pg. 571, 1963.
rat LD50 oral 2315mg/kg (2315mg/kg)   Journal of the American Oil Chemists' Society. Vol. 37, Pg. 40, 1960.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 199 deg C   EXP
log P (octanol-water) 8.690 (none)   EST
Atmospheric OH Rate Constant 2.22E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.