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Product Name: Gossypol
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DC Chemicals Limited
China
Product Name: Gossypol
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Zhejiang Hangyu API Co., Ltd
China
Product Name: GOSSYPOL
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Purity: 99.5%
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Henan Tianfu Chemical Co., Ltd.
China
Product Name: GOSSYPOL 303-45-7
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Purity: 99.0%
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303-45-7

303-45-7 structure

Name: Gossypol
Chemical Name: gossypol
CAS Number: 303-45-7
Molecular Formula: C₃₀H₃₀O₈
Molecular Weight: 518.554
Catalog: API Hormone and endocrine-regulating drugs Birth control pills
Create Date: 2018-04-22 08:00:00
Modify Date: 2024-01-02 04:13:21
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.

Name	gossypol
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

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 Family Research Areas >> Cancer Natural 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.

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

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

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

40817-07-0

~77%

303-45-7

Literature: Li, Ling; Liu, Yuxiu; Wang, Qingmin European Journal of Organic Chemistry, 2013 , # 35 p. 8014 - 8021

784206-41-3

864131-95-3

~73%

303-45-7

Literature: Meltzer; Bickford; Lambert Journal of Organic Chemistry, 1985 , vol. 50, # 17 p. 3121 - 3124

1665-99-2

303-45-7

Literature: European Journal of Organic Chemistry, , # 35 p. 8014 - 8021

499-75-2

303-45-7

Literature: European Journal of Organic Chemistry, , # 35 p. 8014 - 8021

50399-96-7

303-45-7

Literature: European Journal of Organic Chemistry, , # 35 p. 8014 - 8021

1256723-09-7

303-45-7

Literature: European Journal of Organic Chemistry, , # 35 p. 8014 - 8021

17273-29-9

303-45-7

Literature: Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), , # 9 p. 1359 - 1362

73728-76-4

303-45-7

Literature: Chemistry of Natural Compounds, , vol. 26, # 2 p. 129 - 138 Khimiya Prirodnykh Soedinenii, , # 2 p. 166 - 177

7664-93-9

6952-36-9

303-45-7

Literature: Journal of Biological Chemistry, , vol. 76, p. 233

Precursor 7
40817-07-0 864131-95-3 1665-99-2 499-75-2
50399-96-7 73728-76-4 7664-93-9
DownStream 8
21891-57-6 73728-76-4 31591-07-8 64-18-6
64-19-7 79-31-2 82085-03-8 6952-36-9

303-45-7	90141-22-3
77111-05-8	76500-07-7
17337-96-1	5453-04-3
12542-36-8	2744-45-8
11046-16-5	135692-96-5