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12542-36-8

12542-36-8 structure
12542-36-8 structure
Name Gossypol-acetic acid
Synonyms UNII:S7RL72610R
aceticacidgossypol
[2,2'-Binaphthalene]-8,8'-dicarboxaldehyde, 1,1',6,6',7,7'-hexahydroxy-3,3'-dimethyl-5,5'-bis(1-methylethyl)-, compd. with acetic acid (1:1)
1,1',6,6',7,7'-Hexahydroxy-5,5'-diisopropyl-3,3'-dimethyl-2,2'-binaphthalene-8,8'-dicarbaldehyde - acetic acid (1:1)
Acetate gossypol
GOSSYPOLACETATE(GOSSYPOL-ACETICACID)
GOSSYPOL ACETATE
MFCD00058385
Gossypolaceticacidcomplex
GOSSYPOL ACETATE(RG)
UNII:U9GNI6VT5N
1,1',6,6',7,7'-Hexahydroxy-3,3'-dimethyl-5,5'-bis(1-methylethyl)[2,2'-binaphthalene]-8,8'-dicarboxaldehyde-acetic acid
GOSSYPOLMONOACETICACID
Gossypol (acetic acid)
Description Gossypol, a natural product isolated from cottonseeds and roots, binds to Bcl-xL protein and Bcl-2 protein with Kis of 0.5-0.6 μM and 0.2-0.3 mM, respectively.
Related Catalog
Target

Bcl-xL:0.5-0.6 μM (Ki)

Bcl-2:0.2-0.3 mM (Ki)

In Vitro Gossypol, a natural product isolated from cottonseeds and roots that has been studied as an anticancer agent. The racemic form of Gossypol [(±)-Gossypol] is tested in several clinical trials and is well tolerated. The racemic form Gossypol ((±)-Gossypol) binds to Bcl-xL protein with a Ki of 0.5 to 0.6 μM. (±)-Gossypol also potently binds to Bcl-2 protein with a Ki value of 0.2-0.3 mM. The natural racemic Gossypol has two enantiomers, namely the (-)-Gossypol and (+)-Gossypol enantiomers. The racemic form and each of the enantiomers of Gossypol are tested against UM-SCC-6 and UM-SCC-14A in 6-day MTT assays. (-)-Gossypol exhibits greater growth inhibition relative to (±)-Gossypol than (+)-Gossypol in both cell lines tested (P<0.001). An intermediate growth inhibitory effect is observed with (±)-Gossypol but this effect is only observed at the higher dose of Gossypol (10 μM, P<0.0001)[1].
Cell Assay Two representative UM-SCC cell lines, UM-SCC-6 and UM-SCC-14A, are continuously exposed to 0 (vehicle control), 5 or 10 μM (±)-Gossypol, (-)-Gossypol or (+)-Gossypol in a 6-day MTT cell survival assay[1].
References

[1]. Oliver CL, et al. In vitro effects of the BH3 mimetic, (-)-Gossypol, on head and neck squamous cell carcinoma cells. Clin Cancer Res. 2004 Nov 15;10(22):7757-63.
Boiling Point 707.9ºC at 760 mmHg
Melting Point 164-168ºC
Molecular Formula C32H34O10
Molecular Weight 578.606
Flash Point 395.9ºC
Exact Mass 578.215210
PSA 192.82000
LogP 6.47310
Vapour Pressure 1.05E-20mmHg at 25°C

CHEMICAL IDENTIFICATION

RTECS NUMBER :
MD7360000
CHEMICAL NAME :
Gossypol acetic acid
CAS REGISTRY NUMBER :
12542-36-8
LAST UPDATED :
199806

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
282 mg/kg/63W-I
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity)
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
3 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Mammal - cat
DOSE/DURATION :
75 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
1229 mg/kg/4W-I
TOXIC EFFECTS :
Nutritional and Gross Metabolic - weight loss or decreased weight gain Related to Chronic Data - death
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
50 mg/kg/2W-I
TOXIC EFFECTS :
Liver - changes in liver weight Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol) Nutritional and Gross Metabolic - weight loss or decreased weight gain
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
12800 ug/kg
SEX/DURATION :
male 12 week(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
21 mg/kg
SEX/DURATION :
male 75 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
56600 ug/kg
SEX/DURATION :
male 43 week(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
1080 mg/kg
SEX/DURATION :
male 36 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - testes, epididymis, sperm duct Reproductive - Paternal Effects - prostate, seminal vesicle, Cowper's gland, accessory glands Reproductive - Paternal Effects - other effects on male
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
1200 mg/kg
SEX/DURATION :
female 60 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Maternal Effects - menstrual cycle changes or disorders Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
180 mg/kg
SEX/DURATION :
male 24 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Fertility - male fertility index (e.g. # males impregnating females per # males exposed to fertile nonpregnant females)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
10 mg/kg
SEX/DURATION :
female 10 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
1240 mg/kg
SEX/DURATION :
male 62 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count) Reproductive - Fertility - male fertility index (e.g. # males impregnating females per # males exposed to fertile nonpregnant females)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
215 mg/kg
SEX/DURATION :
female 1-5 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
175 mg/kg
SEX/DURATION :
male 7 week(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
1125 mg/kg
SEX/DURATION :
male 45 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - testes, epididymis, sperm duct Reproductive - Paternal Effects - prostate, seminal vesicle, Cowper's gland, accessory glands
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
900 mg/kg
SEX/DURATION :
male 30 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Implant
DOSE :
200 mg/kg
SEX/DURATION :
male 98 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Implant
DOSE :
200 mg/kg
SEX/DURATION :
male 42 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intrauterine
DOSE :
2500 ug/kg
SEX/DURATION :
female 1 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea) Reproductive - Fertility - other measures of fertility
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
1040 mg/kg
SEX/DURATION :
female 1-13 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - other measures of fertility
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
200 mg/kg
SEX/DURATION :
male 20 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count) Reproductive - Paternal Effects - prostate, seminal vesicle, Cowper's gland, accessory glands
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
108 mg/kg
SEX/DURATION :
male 9 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
480 mg/kg
SEX/DURATION :
female 6-13 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
900 mg/kg
SEX/DURATION :
male 90 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
44 mg/kg
SEX/DURATION :
male 11 week(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravaginal
DOSE :
1 mg/kg
SEX/DURATION :
female 1 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Fertility - female fertility index (e.g. # females pregnant per # sperm positive females; # females pregnant per # females mated)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
490 mg/kg
SEX/DURATION :
male 49 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - prostate, seminal vesicle, Cowper's gland, accessory glands
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
630 mg/kg
SEX/DURATION :
male 9 week(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count) Reproductive - Fertility - male fertility index (e.g. # males impregnating females per # males exposed to fertile nonpregnant females)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
420 mg/kg
SEX/DURATION :
male 42 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Fertility - male fertility index (e.g. # males impregnating females per # males exposed to fertile nonpregnant females)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
300 mg/kg
SEX/DURATION :
male 30 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
350 mg/kg
SEX/DURATION :
male 70 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
700 mg/kg
SEX/DURATION :
male 70 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count) Reproductive - Paternal Effects - testes, epididymis, sperm duct Reproductive - Fertility - male fertility index (e.g. # males impregnating females per # males exposed to fertile nonpregnant females)
TYPE OF TEST :
Mutation test systems - not otherwise specified
TYPE OF TEST :
Mutation test systems - not otherwise specified
TYPE OF TEST :
Cytogenetic analysis
TYPE OF TEST :
Sister chromatid exchange

MUTATION DATA

TEST SYSTEM :
Rodent - mouse
DOSE/DURATION :
20 mg/kg
REFERENCE :
TCMUD8 Teratogenesis, Carcinogenesis, and Mutagenesis. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.1- 1980- Volume(issue)/page/year: 6,83,1986
Symbol GHS07 GHS08
GHS07, GHS08
Signal Word Warning
Hazard Statements H302-H351
Precautionary Statements P281
Personal Protective Equipment Eyeshields;full-face particle respirator type N100 (US);Gloves;respirator cartridge type N100 (US);type P1 (EN143) respirator filter;type P3 (EN 143) respirator cartridges
Hazard Codes Xn: Harmful;
Risk Phrases R22;R40
Safety Phrases S22-S36
RIDADR NONH for all modes of transport
WGK Germany 3
RTECS MD7360000
HS Code 2942000000
HS Code 2942000000
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