Gossypol

Modify Date: 2024-01-02 04:13:21

Gossypol Structure
Gossypol structure
 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 Chinese USA Flash Point 395.9±28.0 °C
Symbol GHS08
GHS08		 Signal Word Warning

 Use of Gossypol


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.

 Names

Name gossypol
Synonym More Synonyms

 Gossypol Biological Activity

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.

 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
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

 Synthetic Route

Hemigossypol structure

Hemigossypol

CAS#:40817-07-0

~77%

Gossypol Structure

Gossypol

CAS#:303-45-7
Literature: Li, Ling; Liu, Yuxiu; Wang, Qingmin European Journal of Organic Chemistry, 2013 , # 35 p. 8014 - 8021
N/A structure

N/A

CAS#:784206-41-3
N,N’-diphenylformamidine structure

N,N’-diphenylfo...

CAS#:864131-95-3

~73%

Gossypol Structure

Gossypol

CAS#:303-45-7
Literature: Meltzer; Bickford; Lambert Journal of Organic Chemistry, 1985 , vol. 50, # 17 p. 3121 - 3124
2-HYDROXY-6-ISOPROPYL-METHYL-BENZALDEHYDE structure

2-HYDROXY-6-ISO...

CAS#:1665-99-2

~%

Gossypol Structure

Gossypol

CAS#:303-45-7
Literature: European Journal of Organic Chemistry, , # 35 p. 8014 - 8021
5-Isopropyl-2-methylphenol structure

5-Isopropyl-2-m...

CAS#:499-75-2

~%

Gossypol Structure

Gossypol

CAS#:303-45-7
Literature: European Journal of Organic Chemistry, , # 35 p. 8014 - 8021
4-isopropyl-2,3,8-trimethoxy-6-methyl-1-naphthaldehyde structure

4-isopropyl-2,3...

CAS#:50399-96-7

~%

Gossypol Structure

Gossypol

CAS#:303-45-7
Literature: European Journal of Organic Chemistry, , # 35 p. 8014 - 8021
N/A structure

N/A

CAS#:1256723-09-7

~%

Gossypol Structure

Gossypol

CAS#:303-45-7
Literature: European Journal of Organic Chemistry, , # 35 p. 8014 - 8021
5,5'-Diisopropyl-7,7'-dimethyl-2H,2'H-[8,8']bi[naphtho[1,8-bc]furanyl]-2,3,4,2',3',4'-hexaol structure

5,5'-Diisopropy...

CAS#:17273-29-9

~%

Gossypol Structure

Gossypol

CAS#:303-45-7
Literature: Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), , # 9 p. 1359 - 1362
{[8,8-Bi-3H-naphtho[1,8-bc]furan]-3,} 3-dione, 4,4-dihydroxy-7,7-dimethyl-5,5-bis(1-methylethyl)- structure

{[8,8-Bi-3H-nap...

CAS#:73728-76-4

~%

Gossypol Structure

Gossypol

CAS#:303-45-7
Literature: Chemistry of Natural Compounds, , vol. 26, # 2 p. 129 - 138 Khimiya Prirodnykh Soedinenii, , # 2 p. 166 - 177
Sulfuric acid structure

Sulfuric acid

CAS#:7664-93-9
1-(anilinomethylidene)-7-[8-(anilinomethylidene)-1,6-dihydroxy-3-methyl-7-oxo-5-propan-2-yl-naphthalen-2-yl]-3,8-dihydroxy-6-methyl-4-propan-2-yl-naphthalen-2-one structure

1-(anilinomethy...

CAS#:6952-36-9

~%

Gossypol Structure

Gossypol

CAS#:303-45-7
Literature: Journal of Biological Chemistry, , vol. 76, p. 233

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 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
Top Suppliers:I want be here
  • DC Chemicals Limited
  • China
  • Product Name: Gossypol
  • Price: $250.0/100mg $500.0/250mg $1000.0/1g
  • Purity: 98.0%
  • Stocking Period: 3 Day
  • Contact: Tony Cao

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Price: ￥489/100mg

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17337-96-1
gossypol acetate
5453-04-3
Acetate gossypol
12542-36-8
gossypol acetate
2744-45-8
gossypol acetate
11046-16-5
Gossypol lactone
135692-96-5
Chemsrc provides Gossypol(CAS#:303-45-7) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of Gossypol are included as well.>> amp version: Gossypol

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