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CAS Number: 303-45-7Picture of molecule3D/inchi
Other(deleted CASRN):40112-23-0
Nikkaji Web:J21.393D
Beilstein Number:1917878
XlogP3-AA:6.90 (est)
Molecular Weight:518.56270000
Formula:C30 H30 O8
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
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Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Melting Point: 184.00 °C. @ 760.00 mm Hg
Boiling Point: 707.89 °C. @ 760.00 mm Hg (est)
Flash Point: 745.00 °F. TCC ( 395.90 °C. ) (est)
logP (o/w): 5.419 (est)
Soluble in:
 water, 1.525e-005 mg/L @ 25 °C (est)
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
Cosmetic Information:
None found
Alfa Biotechnology
For experimental / research use only.
Gossypol 98%
BOC Sciences
For experimental / research use only.
Odor: characteristic
Use: Gossypol is an orally-active polyphenolic aldehyde with potential antineoplastic activity. Derived primarily from unrefined cottonseed oil, gossypol induces cell cycle arrest at the G0/G1 phase, thereby inhibiting DNA replication and inducing apoptosis.
Glentham Life Sciences
Santa Cruz Biotechnology
For experimental / research use only.
Sigma-Aldrich: Sigma
For experimental / research use only.
(±)-Gossypol from cotton seeds ≥95% (HPLC)
Safety Information:
Preferred SDS: View
Hazards identification
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
oral-rat LD50 2315 mg/kg
Journal of the American Oil Chemists' Society. Vol. 37, Pg. 40, 1960.

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
Safety in Use Information:
natural substances and extractives
Recommendation for gossypol usage levels up to:
 not for fragrance use.
Recommendation for gossypol flavor usage levels up to:
 not for flavor use.
Safety References:
European Food Safety Authority (EFSA) reference(s):

Presence of free gossypol in whole cottonseed
View page or View pdf

EPI System: View
Daily Med:search
Chemical Carcinogenesis Research Information System:Search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA GENetic TOXicology:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :3503
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
RTECS:DU3100000 for cas# 303-45-7
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):3503
Pubchem (sid):134973612
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
KEGG (GenomeNet):C07667
HMDB (The Human Metabolome Database):HMDB40723
VCF-Online:VCF Volatile Compounds in Food
Potential Blenders and core components note
None Found
Potential Uses:
None Found
Occurrence (nature, food, other):note
 cotton levant cotton seed
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 cotton oil
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 cotton seed
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 okra seed
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 soybean seed
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 sunflower seed
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(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-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-
[2,2'-binaphthalene]-8,8'-dicarboxaldehyde, 1,1',6,6',7,7'-hexahydroxy-3,3'-dimethyl-5,5'-bis(1-methylethyl)-
7-[8-formyl-1,6,7-trihydroxy-3-methyl-5-(methylethyl)(2-naphthyl)]-2,3,8-trihy droxy-6-methyl-4-(methylethyl)naphthalenecarbaldehyde
 gossypol, (±)-isomer


PubMed:Comparative transcriptomic analysis of developing cotton cotyledons and embryo axis.
PubMed:Effectiveness of albumin-conjugated gossypol as an immunogen to prevent gossypol-associated acute hepatotoxicity in rats.
PubMed:(-)-Gossypol-enriched cottonseed oil inhibits proliferation and adipogenesis of human breast pre-adipocytes.
PubMed:Effect of replacing soybean meal protein with protein from upland cottonseed, Pima cottonseed, or extruded Pima cottonseed on production of lactating dairy cows.
PubMed:Impact of antinutritional factors in food proteins on the digestibility of protein and the bioavailability of amino acids and on protein quality.
PubMed:Hemigossypol, a constituent in developing glanded cottonseed (Gossypium hirsutum).
PubMed:Inhibitory effects of gossypol, gossypolone, and apogossypolone on a collection of economically important filamentous fungi.
PubMed:Identification and proteomic analysis of a novel gossypol-degrading fungal strain.
PubMed:Novel O-glycosidic gossypol isomers and their bioactivities.
PubMed:Quercetin downregulates Mcl-1 by acting on mRNA stability and protein degradation.
PubMed:Leptin and zeranol up-regulate cyclin D1 expression in primary cultured normal human breast pre-adipocytes.
PubMed:Gossypol decreases tumor necrosis factor-α-induced intercellular adhesion molecule-1 expression via suppression of NF-κB activity.
PubMed:Aromatase expression in leptin-pretreated human breast pre-adipocytes is enhanced by zeranol and suppressed by (-)-gossypol.
PubMed:Responses of three successive generations of beet armyworm, Spodoptera exigua, fed exclusively on different levels of gossypol in cotton leaves.
PubMed:Spermatotoxicity, biochemical changes and histological alteration induced by gossypol in testicular and hepatic tissues of male rats.
PubMed:Gossypol--a polyphenolic compound from cotton plant.
PubMed:Mutual anti-oxidative effect of gossypol acetic acid and gossypol-iron complex on hepatic lipid peroxidation in male rats.
PubMed:Targeting of cancer energy metabolism.
PubMed:Total and percent atropisomers of gossypol and gossypol-6-methyl ether in seeds from pima cottons and accessions of Gossypium barbadense L.
PubMed:[Determination of gossypol in feeds by HPLC].
PubMed:Bioactivities of gossypol, 6-methoxygossypol, and 6,6'-dimethoxygossypol.
PubMed:Preparation of an edible cottonseed protein concentrate and evaluation of its functional properties.
PubMed:Engineering cottonseed for use in human nutrition by tissue-specific reduction of toxic gossypol.
PubMed:Optimization of process parameters for reduction of gossypol levels in cottonseed meal by Candida tropicalis ZD-3 during solid substrate fermentation.
PubMed:Isolation of 6-methoxy gossypol and 6,6'-dimethoxy gossypol from Gossypium barbadense Sea Island cotton.
PubMed:Ratios of (+)- and (-)-gossypol in leaves, stems, and roots of selected accessions of Gossypium hirsutum var. marie galante (Watt) Hutchinson.
PubMed:Gossypol toxicosis in a dog consequent to ingestion of cottonseed bedding.
PubMed:Effects of source of gossypol and supplemental iron on plasma gossypol in Holstein steers.
PubMed:Occurrence of (+)- and (-)-gossypol in wild species of cotton and in Gossypium hirsutum Var. marie-galante (Watt) Hutchinson.
PubMed:Effects of antinutritional factors on protein digestibility and amino acid availability in foods.
PubMed:Development of competitive direct ELISA for gossypol analysis.
PubMed:[Determination of anti-nutrients in genetically modified crops].
PubMed:[Determination of free gossypol in meat by reversed-phased high performance liquid chromatography].
PubMed:Development of monoclonal antibody-based enzyme-linked immunosorbent assay for gossypol analysis in cottonseed meals.
PubMed:Bollgard II cotton: compositional analysis and feeding studies of cottonseed from insect-protected cotton (Gossypium hirsutum L.) producing the Cry1Ac and Cry2Ab2 proteins.
PubMed:Determination of gossypol enantiomer ratio in cotton plants by chiral higher-performance liquid chromatography.
PubMed:Monoclonal antibodies for the analysis of gossypol in cottonseed products.
PubMed:Irradiation effects on embryotoxicity and oxidative properties of gossypol dissolved in methanol.
PubMed:Toxicity of (+)- and (-)-gossypol to the plant pathogen, Rhizoctonia solani.
PubMed:Feeding cotton products to cattle.
PubMed:Gossypol and gossypolone enantiomers in tissues of rainbow trout fed low and high levels of dietary cottonseed meal.
PubMed:Effects of extrusion temperature and dwell time on aflatoxin levels in cottonseed.
PubMed:Fermentation of cottonseed and other feedstuffs in cattle rumen fluid.
PubMed:Antioxidative effects of cottonseed meals as evaluated in cooked meat.
PubMed:Improved method for the rapid determination of terpenoid aldehydes in cotton.
PubMed:Preference of female students for "tempe" preparations composed of glandless cottonseed and defatted soybean or corn at various ratios.
PubMed:Effect of whole and expanded-expelled cottonseed on milk yield and blood gossypol.
PubMed:Cottonseed with a high (+)- to (-)-gossypol enantiomer ratio favorable to broiler production.
PubMed:Production, characterization, and application of anti-gossypol polyclonal antibodies.
PubMed:Pathological lesions in lambs fed raw or processed cottonseed meal.
PubMed:Environmental inhibition of 11beta-hydroxysteroid dehydrogenase.
PubMed:Effect of coating whole cottonseed on performance of lactating dairy cows.
PubMed:Response of lactating dairy cows to mechanically processed whole cottonseed.
PubMed:The effect of nutrition on chemical toxicity.
PubMed:Alteration of oxytocin-induced calcium oscillations in clone 9 cells by toxin exposure.
PubMed:Infection with Trypanosoma brucei potentiates the antifertility effect of gossypol, especially in the protein-malnourished male rat.
PubMed:Effects on dietary phosphorus of treating cottonseed meal with crystalline ferrous sulphate for the prevention of brown yolk discolouration.
PubMed:Cottonseed protein: what does the future hold?
PubMed:The effect of feeding whole cottonseed on the fertility of bulls.
PubMed:Effects of free gossypol in the diet of pregnant and postpartum Brahman cows on calf development and cow performance.
PubMed:In vitro rat pancreatic digestive enzyme activities and raw and heated glandless cottonseed and soybean flours.
PubMed:Naturally occurring toxins in feedstuffs: Center for Veterinary Medicine Perspective.
PubMed:Allelochemicals in plant foods and feedingstuffs: 1. Nutritional, biochemical and physiopathological aspects in animal production.
PubMed:[Information on advances in sciences and technology. Advances in contraceptive technology].
PubMed:Protection by albumin against the pro-oxidant actions of phenolic dietary components.
PubMed:A stoichiometric analysis of bovine serum albumin-gossypol interactions: a fluorescence quenching study.
PubMed:A review of toxicity factors in some food and feedingstuffs in the nutrition of man and livestock in Nigeria.
PubMed:Iron sulfate and feed pelleting to detoxify free gossypol in cottonseed diets for dairy cattle.
PubMed:Effects of dietary cottonseed meal and iron-treated cottonseed meal in different laying hen genotypes.
PubMed:Incidence and management of poisonings in livestock.
PubMed:Effect of gossypol on thyroid hormones in young female rats.
PubMed:Gossypol residues in organ meats vs thresholds of toxicity.
PubMed:Effects of dietary cottonseed meal, with and without iron treatment, on laying hens.
PubMed:Gossypol as a toxicant in livestock.
PubMed:Failure of oral gossypol to inhibit hepatic microsomal and cytosolic drug-metabolising enzymes.
PubMed:The future of male birth control.
PubMed:Worldwide trends in funding for contraceptive research and evaluation.
PubMed:Spectrophotometric determination of total gossypol in cottonseeds and cottonseed meals.
PubMed:Looking into the future.
PubMed:Detoxification and nutritional evaluation of solvent extracted Egyptian cottonseed meal.
PubMed:Gossypol in cottonseed products: toxicology and inactivation.
PubMed:Gossypol: a possible male antifertility agent. Report of a workshop.
PubMed:Sounding board. The politics of contraception: the view from Beijing.
PubMed:Two food applications of cottonseed flours and meals.
PubMed:Potential for improving cottonseed quality by genetic and agronomic practices.
PubMed:Cottonseed protein derivatives as nutritional and functional supplements in food formulations.
PubMed:Effect of processing on protein utilization by ruminants.
PubMed:[Utilization of gossypol-free cottonseed and its by-products as human food].
PubMed:A comparison of chemical methods for the determination of available lysine in various proteins.
PubMed:Protein products and hulls for animal foods.
PubMed:Fish meal supplementation of chick starting rations containing cottonseed cake.
PubMed:Cottonseed colour fixed pigments. Part II. Role of hexane isomers on oil quality.
PubMed:Effect of free and bound gossypol on the absorption of L-]14-C]lysine, L-[14-C]methionine, and L-[14-C]valine from the rat small intestine.
PubMed:Effect of free gossypol on tissue uptake of iron by everted segments of rat duodenum.
PubMed:Preparation of low-gossypol cottonseed flour.
PubMed:Hematological effects of injected gossypol and iron in rats.
PubMed:[Extraction and precipitation of cottonseed protein by the wet method].
PubMed:Fungal-treated cottonseed meal for swine.
PubMed:Natural non-nutrient substances in the food chain.
PubMed:Effect of gossypol bound to cottonseed protein on growth of weanling rats.
PubMed:[Method of wet concentration of protein of cotton seed cake processed by screw press].
PubMed:Energy value of cottonseed meal for swine.
PubMed:Cottonseed meal, dehydrated grass and ascorbic acid as dietary factors preventing toxicity of vanadium for the chick.
PubMed:Lipid composition of vegetable oils.
PubMed:Effects of dietary iron on gossypol accumulation in and elimination from porcine liver.
PubMed:The in vivo effect of gossypol on cytochrome oxidase, succinoxidase, and succinic dehydrogenase in animal tissues.
PubMed:Effect of single and repeated doses of gossypol on the rat.
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. Constit. of Gossypium hirsutum (cotton)
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