CAS 303-45-7|Gossypol

Introduction：Basic information about CAS 303-45-7|Gossypol, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Gossypol BiologicalActivity
3. Chemical & Physical Properties
4. Toxicological Information
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
MUTATION DATA
5. Safety Information
6. Articles34
7. Synonyms

Common Name	Gossypol
CAS Number	303-45-7	Molecular Weight	518.554
Density	1.4±0.1 g/cm3	Boiling Point	707.9±55.0 °C at 760 mmHg
Molecular Formula	C₃₀H₃₀O₈	Melting Point	181-183ºC
MSDS	ChineseUSA	Flash Point	395.9±28.0 °C
Symbol	GHS08	Signal Word	Warning

Names

Name	gossypol
Synonym	More Synonyms

Gossypol BiologicalActivity

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	Signaling Pathways >>Apoptosis >>Bcl-2 FamilyResearch Areas >>CancerNatural Products >>Phenols
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.

Chemical & Physical Properties

Density	1.4±0.1 g/cm3
Boiling Point	707.9±55.0 °C at 760 mmHg
Melting Point	181-183ºC
Molecular Formula	C₃₀H₃₀O₈
Molecular Weight	518.554
Flash Point	395.9±28.0 °C
Exact Mass	518.194092
PSA	155.52000
LogP	6.16
Vapour Pressure	0.0±2.3 mmHg at 25°C
Index of Refraction	1.742

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: DU3100000

CHEMICAL NAME :: (2,2'-Binaphthalene)-8,8'-dicarboxaldehyde, 1,1',6,6',7,7'-hexahydroxy-5,5'-diisopropyl- 3,3'-dimethyl-

CAS REGISTRY NUMBER :: 303-45-7

BEILSTEIN REFERENCE NO. :: 1917878

LAST UPDATED :: 199803

DATA ITEMS CITED :: 18

MOLECULAR FORMULA :: C30-H30-O8

MOLECULAR WEIGHT :: 518.60

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 2315 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - pig

DOSE/DURATION :: 550 mg/kg

TOXIC EFFECTS :: Behavioral - muscle weakness Gastrointestinal - hypermotility, diarrhea Nutritional and Gross Metabolic - weight loss or decreased weight gain

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 17 mg/kg

SEX/DURATION :: male 60 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 :: 700 mg/kg

SEX/DURATION :: male 35 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 :: 1050 mg/kg

SEX/DURATION :: male 35 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count) Reproductive - Effects on Newborn - live birth index (measured after birth)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 4500 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 :: 525 mg/kg

SEX/DURATION :: male 35 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 :: 700 mg/kg

SEX/DURATION :: male 70 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Fertility - male fertility index (e.g. # males impregnating females per # males exposed to fertile nonpregnant females)

MUTATION DATA

TYPE OF TEST :: Mutation test systems - not otherwise specified

TEST SYSTEM :: Rodent - hamster Ovary

DOSE/DURATION :: 10 mg/L/48H

REFERENCE :: ITCSAF In Vitro. (Rockville, MD) V.1-20, 1965-85. For publisher information, see ICDBEO. Volume(issue)/page/year: 19,53,1983

Safety Information

Symbol	GHS08
Signal Word	Warning
Hazard Statements	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
Risk Phrases	R22;R40
Safety Phrases	S22-S36
RIDADR	NONH for all modes of transport
WGK Germany	3.0
RTECS	DU3100000

Articles34

Male contraception: history and development.

Urol. Clin. North Am. 41(1) , 145-61, (2014)

Although the twentieth century has seen great strides in the development of female contraception, not a single new agent has been introduced as an approved method for common use for male contraception...

The investigational agent MLN2238 induces apoptosis and is cytotoxic to CLL cells in vitro, as a single agent and in combination with other drugs.

Br. J. Haematol. 165(1) , 78-88, (2014)

Chronic lymphocytic leukaemia (CLL) is the most common haematological malignancy in the U.S. The course of the disease has been shown to be negatively impacted by increased levels of BCL2. Strategies ...

(-)-Gossypol-enriched cottonseed oil inhibits proliferation and adipogenesis of human breast pre-adipocytes.

Anticancer Res. 33(3) , 949-55, (2013)

Breast cancer is the most commonly diagnosed cancer in women. Obesity is an important risk factor for developing breast cancer and is one of few risk factors that women can modify to prevent cancer. (...

Synonyms

MFCD00017352

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-5,5'-diisopropyl-3,3'-dimethyl-2,2'-binaphthalene-8,8'-dicarbaldehyde

2,2'-BI[8-FORMYL-1,6,7-TRIHYDROXY-5-ISOPROPYL-3-METHYLNAPHTHALENE]

2,2'-Bis[1,6,7-trihydroxy-3-methyl-5-isopropyl-8-aldehydonaphthalene]

1,1',6,6',7,7'-hexahydroxy-3,3'-dimethyl-5,5'-di(propan-2-yl)-2,2'-binaphthalene-8,8'-dicarbaldehyde

Gossypol

gossypol from cotton seeds

(rac)-2,2'-bis(8-formyl-1,6,7-trihydroxy-5-isopropyl-3-methylnaphthalene)

2,2'-bis[8-formyl-1,6,7-trihydroxy-5-isopropyl-3-methylnaphthalene]

(-)-1,1',6,6',7,7'-Hexahydroxy-3,3'-dimethyl-5,5'-bis(1-methylethyl)[2,2'-binaphthalene]-8,8'-dicarboxaldehyde

2,2'-BIS[8-FORMYL-1,6,7-TRIHYDROXY-5-ISOPROPYL-3-METHYLNAPTHALENE]

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-5,5'-diisopropyl-3,3'-dimethyl-2,2'-binaphthalen-8,8'-dicarbaldehyd

Thespesin

[2,2'-Binaphthalene]-8,8'-dicarboxaldehyde, 1,1',6,6',7,7'-hexahydroxy-3,3'-dimethyl-5,5'-bis(1-methylethyl)-

1,1',6,6',7,7'-hexahydroxy-3,3'-dimethyl-5,5'-bis(1-methylethyl)-2,2'-binaphthalene-8,8'-dicarbaldehyde

roduct Name

(+/-)-gossypol

1,1',6,6',7,7'-Hexahydroxy-3,3'-dimethyl-5,5'-bis(1-methylethyl)[2,2'-binaphthalene]-8,8'-dicarboxaldehyde

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