1,1’,6,6’,7,7’-Hexahydroxy-5,5’-Diisopropyl-3,3’-Dimethyl-[2,2’-Binaphthalene]-8,8’-Dicarbaldehyde 1,1’,6,6’,7,7’-六羟基-5,5’-二异丙基-3,3’-二甲基-[2,2’-联萘]-8,8’-二甲醛
CAS 303-45-7 MFCD00017352
化学结构图
SMILES: Cc1cc2c(C(C)C)c(O)c(O)c(C=O)c2c(O)c1-c1c(C)cc2c(C(C)C)c(O)c(O)c(C=O)c2c1O
化学属性
| Mol. Formula | C30H30O8 |
|---|---|
| Mol. Weight | 518.55 |
| Solubility | Soluble in 100%ethanol (25 mg/ml), DMF (25 mg/ml), acetone, DMSO (25 mM), methanol (2 mg/ml), ether, chloroform, sodium carbonate, and dilute aqueous solutions of ammonia . Insoluble in water. |
别名和识别编码
| Chemical Name | 1,1’,6,6’,7,7’-Hexahydroxy-5,5’-Diisopropyl-3,3’-Dimethyl-[2,2’-Binaphthalene]-8,8’-Dicarbaldehyde |
|---|---|
| MDL Number | MFCD00017352 |
| PubChem Substance ID | 3503 |
| CAS Number | 303-45-7 |
| Chemical Name Translation | 1,1’,6,6’,7,7’-六羟基-5,5’-二异丙基-3,3’-二甲基-[2,2’-联萘]-8,8’-二甲醛 |
| Beilstein Registry Number | 1917878 |
| Synonym | (±)-2,2′-Bis(8-formyl-1,6,7-trihydroxy-5-isopropyl-3-methylnaphthalene) Dipotassium Salt, Gossypol Gossypol Gossypol Dipotassium Salt Gossypol Sodium Salt Gossypol, (+)-Isomer Gossypol, (+-)-Isomer Gossypol, (-)-Isomer Sodium Salt, Gossypol |
| LabNetwork Molecule ID | LN01294486 |
| InChI | InChI=1S/C30H30O8/c1-11(2)19-15-7-13(5)21(27(35)23(15)17(9-31)25(33)29(19)37)22-14(6)8-16-20(12(3)4)30(38)26(34)18(10-32)24(16)28(22)36/h7-12,33-38H,1-6H3 |
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分类
- {SNA} Aldehydes,
- {SA} Aerobic Glycolysis (the Warburg Effect), Aldehydes, Bioactive Small Molecules, Building Blocks, C13-C60, Cancer Metabolism, Cancer Research, Carbonyl Compounds, Cell Biology, Cell Signaling and Neuroscience, Cell Stress, Chemical Synthesis, G, Inhibitors of Aerobic Glycolysis (the Warburg Effect), Lactate Dehydrogenase Inhibitors, Nitric Oxide and Cell Stress, Organic Building Blocks, Oxidative Stress Proteins and Reagents
- {SNA} Aerobic Glycolysis (the Warburg Effect), Aldehydes, Bioactive Small Molecules, Building Blocks, C13-C60, Cancer Metabolism,
- {SNA} Aldehydes,
产品应用
- An inhibitor of PKC, Bcl-2, 5-LO, and 12-LO.
相关文献及参考
- Kovacic, P., Mechanism of drup and toxic actions of gossypol; forcus on reactive oxygen species and electron transfer. Curr. Med. Chem. 10 , 2711-2718, (2003) 摘要
- Merck 14 ,4528
安全信息
GHS Symbol
- P201 Obtain special instructions before use. 使用前获取专门指示。
- P202 Do not handle until all safety precautions have been read and understood. 已阅读并理解所有的安全预防措施之前，切勿操作。
- P281 Use personal protective equipment as required. 使用所需的个人防护装备。
- P308+P313
- P405 Store locked up. 上锁保管。
- P501 Dispose of contents/container to..… 处理内容物/容器.....
- H351 Suspected of causing cancer 怀疑致癌
- S22 Do not breathe dust 不要吸入粉尘；
- S36 Wear suitable protective clothing 穿戴适当的防护服；
- R22 Harmful if swallowed 吞咽有害
- R40 Limited evidence of a carcinogenic effect 有限证据表明其致癌作用
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 REFERENCE : JAOCA7 Journal of the American Oil Chemists' Society. (Champaign, IL) V.24-56, 1947-79. Volume(issue)/page/year: 40,571,1963
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 REFERENCE : JAOCA7 Journal of the American Oil Chemists' Society. (Champaign, IL) V.24-56, 1947-79. Volume(issue)/page/year: 37,40,1960
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
TYPE OF TEST : Cytogenetic analysis TEST SYSTEM : Human - man Lymphocyte DOSE/DURATION : 9 ug/plate REFERENCE : CPHPA5 Jiepou Xuebao. Journal of Anatomy. (China International Book Trading Corp., POB 2820, Beijing, Peop. Rep. China) V.1-9, 1953-66; V.10- 1979- Volume(issue)/page/year: 12,293,1981
TYPE OF TEST : DNA inhibition TEST SYSTEM : Rodent - hamster Ovary DOSE/DURATION : 10 mg/L REFERENCE : ITCSAF In Vitro. (Rockville, MD) V.1-20, 1965-85. For publisher information, see ICDBEO. Volume(issue)/page/year: 19,53,1983
TYPE OF TEST : Mutation test systems - not otherwise specified TEST SYSTEM : Rodent - hamster Ovary DOSE/DURATION : 50 mg/L REFERENCE : ITCSAF In Vitro. (Rockville, MD) V.1-20, 1965-85. For publisher information, see ICDBEO. Volume(issue)/page/year: 19,53,1983
TYPE OF TEST : DNA inhibition TEST SYSTEM : Human HeLa cell DOSE/DURATION : 10 mg/L REFERENCE : CNREA8 Cancer Research. (Public Ledger Building, Suit 816, 6th & Chestnut Sts., Philadelphia, PA 19106) V.1- 1941- Volume(issue)/page/year: 44,35,1984
TYPE OF TEST : Sister chromatid exchange TEST SYSTEM : Human - man Lymphocyte DOSE/DURATION : 1 ug/plate REFERENCE : CPHPA5 Jiepou Xuebao. Journal of Anatomy. (China International Book Trading Corp., POB 2820, Beijing, Peop. Rep. China) V.1-9, 1953-66; V.10- 1979- Volume(issue)/page/year: 12,293,1981
TY
TYPE OF TEST : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE : Oral
SPECIES OBSERVED : Human - man
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)
REFERENCE :
CMJODS Chinese Medical Journal (Beijing, English Edition). (China
International Book Trading Corp., POB 2820, Beijing, Peop. Rep. China) V.1-
1975- Adopted vol. no. 92 in 1979. Volume(issue)/page/year: 4,417,1978TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Primate - monkey 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) REFERENCE : ARANDR Archives of Andrology. (Elsevier Science Pub. Co., Inc., 52 Vanderbilt Ave., New York, NY 10017) V.1- 1978- Volume(issue)/page/year: 13,199,1984
TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - rat 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) REFERENCE : NFGZAD Nippon Funin Gakkai Zasshi. Japanese Journal of Fertility and Sterility. (Nippon Funin Gakkai, 1-1 Sadohara-cho, Ichigaya, Shinjuku-ku, Toyko 162, Japan) V.1- 19
TYPE
其他信息
- Gossypol is a male antifertility agent with antispermatogenic activity and has been shown to contain anitumor, anitviral, and antioxidant properties. Gossypol is a reversible inhibitor of PP2B (protein phosphatase 2B), mitotic kinesin Eg5, and PKC (protein kinase C). Gossypol also potentially inhibits PAF-R, Bcl-2, 5-LO (5-lipoxygenase), 12-LO, and leukotriene-induced guinea pig parenchyma contractions. Gossypol is an inhibitor of Bcl-xl, PKD and p107.
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