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303-45-7

303-45-7 structure
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: 2025-08-21 13:01:59
  • 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
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
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 structure

40817-07-0

~77%

303-45-7 structure

303-45-7

Literature: Li, Ling; Liu, Yuxiu; Wang, Qingmin European Journal of Organic Chemistry, 2013 , # 35 p. 8014 - 8021
784206-41-3 structure

784206-41-3

864131-95-3 structure

864131-95-3

~73%

303-45-7 structure

303-45-7

Literature: Meltzer; Bickford; Lambert Journal of Organic Chemistry, 1985 , vol. 50, # 17 p. 3121 - 3124
1665-99-2 structure

1665-99-2

~%

303-45-7 structure

303-45-7

Literature: European Journal of Organic Chemistry, , # 35 p. 8014 - 8021
499-75-2 structure

499-75-2

~%

303-45-7 structure

303-45-7

Literature: European Journal of Organic Chemistry, , # 35 p. 8014 - 8021
50399-96-7 structure

50399-96-7

~%

303-45-7 structure

303-45-7

Literature: European Journal of Organic Chemistry, , # 35 p. 8014 - 8021
1256723-09-7 structure

1256723-09-7

~%

303-45-7 structure

303-45-7

Literature: European Journal of Organic Chemistry, , # 35 p. 8014 - 8021
17273-29-9 structure

17273-29-9

~%

303-45-7 structure

303-45-7

Literature: Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), , # 9 p. 1359 - 1362
73728-76-4 structure

73728-76-4

~%

303-45-7 structure

303-45-7

Literature: Chemistry of Natural Compounds, , vol. 26, # 2 p. 129 - 138 Khimiya Prirodnykh Soedinenii, , # 2 p. 166 - 177
7664-93-9 structure

7664-93-9

6952-36-9 structure

6952-36-9

~%

303-45-7 structure

303-45-7

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