TIMTEC-BB SBB012338
gossypol
CAS: 303-45-7
Molecular Formula: C30H30O8
TIMTEC-BB SBB012338 - Names and Identifiers
| Name | gossypol |
| Synonyms | gossypol GOSSYPOL Thespesin NSC 56817 NSC 624336 GOSSYPOL(P) TIMTEC-BB SBB012338 GOSSYPOL, COTTON SEEDS 2,2'-BIS[8-FORMYL-1,6,7-TRIHYDROXY-5-ISOPROPYL-3-METHYLNAPTHALENE] 2,2'-BI[8-FORMYL-1,6,7-TRIHYDROXY-5-ISOPROPYL-3-METHYLNAPHTHALENE] 2,2'-BIS[8-FORMYL-1,6,7-TRIHYDROXY-5-ISOPROPYL-3-METHYLNAPHTHALENE] 2,2'-bis(1,6,7-trihydroxy-3-methyl-5-isopropyl-8-aldehydonaphthalene) Gossypol from cotton seeds,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 |
| CAS | 303-45-7 |
| EINECS | 636-899-7 |
| InChI | InChI=1/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 |
| InChIKey | QBKSWRVVCFFDOT-UHFFFAOYSA-N |
TIMTEC-BB SBB012338 - Physico-chemical Properties
| Molecular Formula | C30H30O8 |
| Molar Mass | 518.55 |
| Density | 1.1912 (rough estimate) |
| Melting Point | 181-183 C |
| Boling Point | 522.63°C (rough estimate) |
| Water 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. Gossypo |
| Solubility | Very slightly soluble in petroleum ether, easily soluble in dilute sodium carbonate and carbonic acid aqueous solution, soluble in methanol, ethanol, ether, chloroform and dimethylformamide, insoluble in water. |
| Appearance | Yellow crystal |
| pKa | 7.15±0.50(Predicted) |
| Storage Condition | 2-8°C |
| Refractive Index | 1.4900 (estimate) |
| MDL | MFCD00017352 |
| Physical and Chemical Properties | Storage Conditions 2-8°C |
| In vitro study | 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 K i of 0.5 to 0.6 μM. (±)-Gossypol also potently binds to Bcl-2 protein with a K i 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). |
TIMTEC-BB SBB012338 - Risk and Safety
| Risk Codes | R22 - Harmful if swallowed R40 - Limited evidence of a carcinogenic effect R36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S22 - Do not breathe dust. S36 - Wear suitable protective clothing. S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. S27 - Take off immediately all contaminated clothing. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. |
| WGK Germany | 3 |
| RTECS | DU3100000 |
| HS Code | 29124990 |
| Toxicity | A secondary plant product produced by some varieties of cotton and found in cottonseed meal and cottonseed oil from those varieties. Affects the male reproductive system and has potential use as a male contraceptive agent. May be irritating to the GI tract. In animal studies large doses caused lung edema and paralysis. |
TIMTEC-BB SBB012338 - Reference
| Reference Show more | 1. Suixiu, Xie, Quanxi, Chen Zhen, et al. Degradation of gossypol in cottonseed meal by neutral protease [J]. China brewing 2017 036(010):144-148. 2. Suixiu, Xie Quanxi, Liu naizhi, etc. Determination of gossypol by high performance liquid chromatography and comparison of different gossypol detoxification methods [J]. China feed, 2019. 3. Yunxiu, Xie Quanxi, Yu Jiamin, etc. Screening of free gossypol-degrading strains from cottonseed meal and optimization of complex fermentation method [J]. Chinese Journal of cereal and oil, 2019, 034(001):99-106. 4. Yunxiu, Xie Quanxi, Chen Zhen, Yu Jiamin, Xu Haiyan, Gu Wei. Screening of strains for efficient degradation of free gossypol and improvement of nutritional quality of cottonseed meal [J]. Chinese Journal of Animal Nutrition, 2017,29(09):3258-3266. 5. Yunxiu, Xie Quanxi, Yu Jiamin, etc. Identification, safety evaluation and fermentation process of a strain with high degradation efficiency of free gossypol [J]. Modern food science and technology, 2018(5). |
TIMTEC-BB SBB012338 - Reference Information
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| introduction | gossypol (gossypol), also known as cotton toxin or cottonseed alcohol, is a yellow polyphenol dinaphthalene compound formed in cotton plants. |
| biological activity | Gossypol (BL 193) is an orally active polyphenol isolated from cottonseed and root. Gossypol is an effective inhibitor of 5α-reductase 1 and 3α-hydroxysteroid dehydrogenase. In the cell-free test, the corresponding IC50 values are 3.33 μM and 0.52 μM respectively. Gossypol can also inhibit the binding of BH3 peptide to Bcl protein, and the IC50 values for Bcl-XL and Bcl-2 are 0.4 μM and 10 μM respectively. Gossypol can induce apoptosis and cell growth inhibition in various cancer cells. |
| Target | Value |
| Bcl-xL (Cell-free assay) | 0.4 μM |
| 3α-hydroxysteroid dehydrogenase (Cell-free assay) | 0.52 μM |
| 5α-reductase 1 (Cell-free assay) | 3.33 μM |
| Bcl-2 (Cell-free assay) | 10 μM |
| use | gossypol has anti-tumor effect and can be used as a male contraceptive. |
| category | toxic substances |
| toxicity classification | highly toxic |
| acute toxicity | oral administration-rat LD50: 325 mg/kg; Oral administration-mouse LD50: 765 mg/m3/4 h |
| flammability hazard characteristics | combustible, spicy and irritating smoke from the fire site |
| storage and transportation characteristics | warehouse is low temperature, ventilated and dry; Store separately from food raw materials |
| fire extinguishing agent | water, carbon dioxide, dry powder, sand |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 21:11:58
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View History
TIMTEC-BB SBB012338
2-氨基-4-甲基噻唑-5-甲酸甲脂
17α-Hydroxycortexone 21-acetate
Methyl[(Dimethoxyphosphinothioyl)thio]acetate
6α-甲基强的松龙
HPCG
Phosphorylase b from rabbit muscle
匹莫范色林 PRM
180869-39-0
2-氨基-4-甲基噻唑-5-甲酸甲脂
17α-Hydroxycortexone 21-acetate
Methyl[(Dimethoxyphosphinothioyl)thio]acetate
6α-甲基强的松龙
HPCG
Phosphorylase b from rabbit muscle
匹莫范色林 PRM
180869-39-0