GOSSYPOL

2,2'-Bis(1,6,7-trihydroxy-3-methyl-5-isopropyl-8-aldehydonaphthalene); 8-Formyl-1,6,7-trihydroxy-5- isopropyl- 3-methyl-2,2'-bisnaphthalene; 1,1',6,6',7,7'-Hexahydroxy-5,5'-diisopropyl-3,3'-dimethyl -(2,2'-binaphthalene)-8,8'-dicarboxaldehyde; 2,2'-bis(8-Formyl-1,6,7-trihydroxy-5-isopropyl-3- methylnaphthalene); 7-(8-Formyl-1,6,7-trihydroxy-3-methyl-5-propan-2-ylnaphthalen-2-yl)-2,3, 8-trihydroxy- 6-methyl-4-propan-2-ylnaphthalene-1-carbaldehyde

GOSSYPOL

 

PRODUCT IDENTIFICATION

CAS RN

303-45-7

EINECS RN

 

FORMULA

C30H30O8

MOLE WEIGHT

518.55

 

PHYSICAL AND CHEMICAL PROPERTIES

PHYSICAL STATE

white to yellow crystalline powder

MELTING POINT

177 - 182 C

BOILING POINT

 

DENSITY

 

SOLUBILITY IN WATER

 

pH

 

VAPOR DENSITY

 

REFRACTIVE INDEX

 

FLASH POINT

 

 

STABILITY AND REACTIVITY
STABILITY Stable under normal conditions

INCOMPATIBLE MATERIALS

Strong oxidizing agents.

DECOMPOSITION PRODUCTS

Carbon oxides.

POLYMERIZATION Has not been reported

NFPA RATINGS

Health: 1, Flammability: 0, Reactivity: 0

 

SAFETY

HAZARD NOTES

Target Organ Effect. Target Organs: Male reproductive system.

EYE

May cause eye irritation.

SKIN

May be harmful if absorbed through skin. May cause skin irritation.

INGESTION

May be harmful if swallowed.

INHALATION

May be harmful if inhaled. May cause respiratory tract irritation.

CHRONIC

 

 

TRANSPORT & REGULATORY INFORMATION

UN NO.

 
HAZARD CLASS

 

PACKING GROUP

 

HAZARD CODE

XN

RISK STATEMENTS

22-40

SAFETY STATEMENTS

22-36

 

EXTERNAL LINKS & GENERAL INFORMATION

Gossypol is a poisonous pigment found in cottonseed and its name is derived from the botanical name of the cotton plant, Gossypium L, Malvaceae. The toxicity of gossypol is shown against the reproductive system, heart, liver, and membranes. The compound exhibits both pro- and anti-oxidant behavior. Electron transfer (ET) functionalities, present in gossypol and its metabolites, comprise conjugated dicarbonyl, a quinone derivative, Schiff bases, and metal complexes. The parent possesses a reduction potential favorable for in vivo ET. Considerable evidence points to oxidative stress, formation of a reactive oxygen species, and DNA scission, characteristics of redox cycling by ET in biosystems, as mechanism of action for gossypol. In a study on the apoptotic effect of gossypol on human lymphocytes, gossypol was used at 20-50 mM to induce apoptosis in human lymphocytes without causing necrosis through cytotoxic effects. The combined use of steroid hormones (methyltestosterone and ethinyl estradiol) and gossypol (low dose) in an antifertility study in rats showed that the steroid hormone made the procedure of spermatogenesis slower and low dose gossypol caused all sperm to lose their activity in the epididymis. Both affect the process of spermatogenesis from different endpoints and successfully induce infertility in the short term. A low dose of gossypol not only executes antifertility function in the epididymis, but also affects the quality of spermatozoal production in testis by impacting the procedures of both acrosomal formation and spermatozoal elongation. This assists in maintaining long term infertility. Gossypol, as a PAF antagonist/inhibitor, markedly inhibited the contractile responses of guinea-pig lung parenchyma strips stimulated with leukotriene B4, leukotriene D4, and PAF-acether. It was suggested that the inhibition of the myotropic activity of the lung parenchyma by gossypol is due to interactions with the formation of cyclooxygenase products within  the guinea-pig lung. (http://www.sigmaaldrich.com/)

Gossypol is a chemical found in the seeds of cotton plants. Cotton plants produce gossypol in order to slow down the reproduction of the insects that eat cotton bolls and seeds; the compound also affects reproduction in mammals. Pressed cakes of cotton seeds, a byproduct of the cotton industry, are sometimes fed to livestock with unintentional contraceptive effects. The effect of gossypol on human male fertility has been known in China for many years. In 1929, a study of couples who used crude cottonseed oil for cooking showed that they had smaller than average families. Specifically, researchers showed that the oil affected male fertility. Eventually researchers isolated the contraceptive compound gossypol from the cotton seed oil. This discovery led to large scale testing of gossypol as a male contraceptive in China during the 1970s. The studies involved over 8,000 men, and continued for over a decade. The researchers found that men taking a daily gossypol pill had reliable contraception and no complaints about change in libido. However, the studies revealed two serious flaws: disruption of potassium uptake and incomplete reversibility. (http://www.malecontraceptives.org/)

Gossypol is a dimeric or bis-naphthalene natural product isolated from the seeds of cotton plants (various Gossypium species). The naphthalene rings, however, are derived from sesquiterpenes of the cadinane family. The cadinanes are formed in the biogenetic cascade from the bisabolane intermediate by a series of putative 1,2-shifts and cyclization. The interest in gossypol derives from its activity as a contraceptive in human males. It has been shown to affect the maturation and motility of sperm, and it inactivates the enzymes required for the sperm to fertilize the ova. Gossypol has been used clinically in China and the contraceptive effect has been shown to be reversible in short term usage. Gossypol also has been found to have antiviral, antiherpes, antipsoriasis, antikeratitus, and antineoplastic activity. Gossypol exists as two atropisomers due to restricted rotation about the biaryl bond. The contraceptive effect appears to be associated with the (-)-isomer, while toxic effects (cardiac toxicity in cattle) appear to be associated with the (+)-isomer. (http://www.people.vcu.edu/)

 

Contraceptive agents

Product

CAS RN.

5-Thio-D-glucose 20408-97-3
Algestone acetophenide 24356-94-3
Algestone 595-77-7
Anordiol 1045-30-3
Anordrin 56470-64-5
Bisecurin I 8056-92-6
Centchroman 31477-60-8
Chlormadinone acetate 302-22-7
Chlormadinone Acetate 302-22-7
Cloprostenol 40665-92-7
Cyproterone acetate 427-51-0
Desogestrel 54024-22-5
Diallyl disulfide 2179-57-9
Diallyl trisulfide 2050-87-5
Dienogest 65928-58-7
Dimethisterone 79-64-1

Estradiol benzoate

50-50-0

Estradiol cypionate 313-06-4
Estradiol valerate 979-32-8
Estropipate 7280-37-7
Ethinyl estradiol 57-63-6
Ethynodiol diacetate 297-76-7
Etonogestrel 54048-10-1
Fluprostenol 40666-16-8
Gestodene 60282-87-3
Gestrinone 16320-04-0
Gossypol acetic acid 12542-36-8
Gossypol 303-45-7
Levonorgestrel 797-63-7

L-Norgestrel

17489-40-6

Lonidamine 50264-69-2
Lynestrenol 52-76-6
Medroxyprogesterone acetate 71-58-9
Medroxyprogesterone 520-85-4
Megestrol 3562-63-8
Mestranol 72-33-3
Mifepristone 84371-65-3
Molinate 2212-67-1
Neem oil 8002-65-1
Nestorone 7759-35-5
Nonoxynol 15 26027-38-3
Norelgestromin 53016-31-2
Norethindrone enanthate 3836-23-5
Norethindrone acetate 51-98-9
Norethindrone 68-22-4
Norethynodrel 68-23-5
Norgestimate 35189-28-7
Norgestrel 6533-00-2
Norgestrienone 848-21-5
Octoxynol 9 9002-93-1
p-Coumaric acid 7400-08-0
Plumbagin 481-42-5
Polyethylene glycol octylphenyl ether 9036-19-5

Progesterone

57-83-0

Sodium polystyrene sulfonate 37349-16-9
Sulprostone 60325-46-4
Trestolone 3764-87-2
Triptolide 38748-32-2
Triptorelin 57773-63-4

 

SALES SPECIFICATION

APPEARANCE

white to yellow crystalline powder

ASSAY

95.0% min (HPLC)

HEAVY METAL

20ppm max

ARSENIC

1ppm max

LEAD

2ppm max

MICROBIOLOGY

Total Plate Count:1000cfu/g
Yeast and Mold: 100cfu/g
E.Coli: Negative
Salmonella: Negative

RESIDUAL SOLVENTS

pass EP.2000 (Water and Alcohol)

SIEVE ANALYSIS

80 mesh (100%)

 

PRICE INFORMATION

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