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Name |
Gossypol |
EINECS | 636-899-7 |
CAS No. | 303-45-7 | Density | 1.403 g/cm3 |
PSA | 155.52000 | LogP | 6.38220 |
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. Gossypol is a male antifertility agent with antispermatogenic activity and has been shown to contain antitumor, anitviral, and antioxidant properties. | Melting Point |
181-183 °C |
Formula | C30H30O8 | Boiling Point | 707.888 °C at 760 mmHg |
Molecular Weight | 518.563 | Flash Point | 395.872 °C |
Transport Information | N/A | Appearance | N/A |
Safety | 22-36-36/37/39-27-26 | Risk Codes | 22-40-36/37/38 |
Molecular Structure | Hazard Symbols | Xi, Xn | |
Synonyms |
[2,2'-Binaphthalene]-8,8'-dicarboxaldehyde,1,1',6,6',7,7'-hexahydroxy-5,5'-diisopropyl-3,3'-dimethyl- (8CI);1,1',6,6',7,7'-Hexahydroxy-5,5'-diisopropyl-3,3'-dimethyl-2,2'-binaphthalene-8,8'-dicarboxaldehyde;1,6,7,1',6',7'-Hexahydroxy-5,5'-diisopropyl-3,3'-dimethyl-[2,2']binaphthalenyl-8,8'-dicarboxaldehyde;2,2'-Bis[1,6,7-trihydroxy-3-methyl-5-isopropyl-8-aldehydonaphthyl];2,2'-Bis[8-formyl-1,6,7-trihydroxy-5-isopropyl-3-methylnaphthyl];BL 193;NSC 56817;NSC 624336;No Fertil;Pogosin;Tash 1; |
Article Data | 16 |
(±)-gossypol acetic acid
(rac)-gossypol
Conditions | Yield |
---|---|
With iron(III) chloride In acetone at 60℃; | 85% |
In diethyl ether; water at 25℃; for 0.166667h; Temperature; Solvent; Sonication; | 105 mg |
2,3,8-trihydroxy-4-isopropyl-6-methyl-1-naphthaldehyde
(rac)-gossypol
Conditions | Yield |
---|---|
With tert-butyl peroxyacetate In 1,2-dichloro-ethane at 80℃; for 4h; Inert atmosphere; | 76.1% |
With tert-butyl peroxyacetate In 1,2-dichloro-ethane at 80℃; for 2.5h; Temperature; Inert atmosphere; | 52% |
With tert-butyl peroxyacetate In 1,2-dichloro-ethane; mineral oil at 80℃; for 2.5h; Inert atmosphere; Schlenk technique; | 41% |
With laccase of Coriolus versicolor; oxygen at 30℃; pH=5.5; aq. phosphate buffer; |
Conditions | Yield |
---|---|
With hydroquinone at 180℃; under 5 - 15 Torr; for 2.5h; | 72% |
apogossypol
(rac)-gossypol
Conditions | Yield |
---|---|
With Dichloromethyl methyl ether; titanium tetrachloride In dichloromethane at 0 - 20℃; for 5h; Inert atmosphere; | 37% |
4,4'-dihydroxy-5,5'-diisopropyl-7,7'-dimethyl-bis(3H-naphtho[1,8-bc]furan-3-one)
(rac)-gossypol
Conditions | Yield |
---|---|
In water; acetone for 48h; |
(rac)-gossypol
Conditions | Yield |
---|---|
With hydrogenchloride In ethanol at 25℃; Kinetics; Mechanism; Thermodynamic data; other temperatures, ΔH(excit.), ΔS(excit.), ΔG(excit.); |
(rac)-gossypol
Conditions | Yield |
---|---|
With hydrogenchloride; acetic acid In diethyl ether Heating; |
(rac)-gossypol
Conditions | Yield |
---|---|
With hydrogenchloride; acetic acid In diethyl ether Heating; |
(rac)-gossypol
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: silver(l) oxide / methanol / 3 h / 20 °C 2: potassium carbonate / acetone / 5 h / 20 °C 3: dichloromethane / 0.5 h / 20 °C 4: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C 5: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C 6: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere 7: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 7 steps 1: silver(l) oxide / 2 h / Reflux 2: potassium carbonate / acetone / 5 h / 20 °C 3: dichloromethane / 0.5 h / 20 °C 4: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C 5: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C 6: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere 7: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 8 steps 1: silver(l) oxide / methanol / 3 h / 20 °C 2: potassium carbonate / acetone / 5 h / 20 °C 3: dichloromethane / 0.5 h / 20 °C 4: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C 5: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C 6: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere 7: hydrogenchloride / water; acetonitrile / 5 h / 20 °C 8: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 8 steps 1: silver(l) oxide / 2 h / Reflux 2: potassium carbonate / acetone / 5 h / 20 °C 3: dichloromethane / 0.5 h / 20 °C 4: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C 5: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C 6: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere 7: hydrogenchloride / water; acetonitrile / 5 h / 20 °C 8: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere View Scheme |
EPA Genetic Toxicology Program.
The Gossypol, with the CAS registry number 303-45-7, is also known as 2,2'-Bis(8-Formyl-1,6,7-trihydroxy-5-isopropyl-3-methylnaphthalene). It belongs to the product categories of Aromatic Phenols; Antitumour. This chemical's molecular formula is C30H30O8 and molecular weight is 518.55. What's more, its IUPAC name is called 7-(8-Formyl-1,6,7-trihydroxy-3-methyl-5-propan-2-ylnaphthalen-2-yl)-2,3,8-trihydroxy-6-methyl-4-propan-2-ylnaphthalene-1-carbaldehyde. Gossypol is a natural phenol derived from the cotton plant (genus Gossypium). Gossypol is a phenolic aldehyde that permeates cells and acts as an inhibitor for several dehydrogenase enzymes. It is a yellow pigment. And this chemical should be kept in a cold, dry place.
Physical properties about Gossypol are: (1)ACD/LogP: 5.42; (2)# of Rule of 5 Violations: 3; (3)ACD/LogD (pH 5.5): 5.405; (4)ACD/LogD (pH 7.4): 4.795; (5)ACD/BCF (pH 5.5): 7488.263; (6)ACD/BCF (pH 7.4): 1838.539; (7)ACD/KOC (pH 5.5): 20462.531; (8)ACD/KOC (pH 7.4): 5024.019; (9)#H bond acceptors: 8; (10)#H bond donors: 6; (11)#Freely Rotating Bonds: 11; (12)Polar Surface Area: 155.52 Å2; (13)Index of Refraction: 1.742; (14)Molar Refractivity: 149.345 cm3; (15)Molar Volume: 369.555 cm3; (16)Surface Tension: 71.297 dyne/cm; (17)Density: 1.403 g/cm3; (18)Flash Point: 395.872 °C; (19)Enthalpy of Vaporization: 107.239 kJ/mol; (20)Boiling Point: 707.888 °C at 760 mmHg; (21)Vapour Pressure: 0 mmHg at 25 °C.
Preparation of Gossypol: it is a polyphenol derived from the cotton plant (genus Gossypium, family Malvaceae). It is formed metabolically through acetate via the isopernoid pathway.
Uses of Gossypol: it is used to produce other chemicals. For example, it can react with Ethylamine to get 1,6,7,1',6',7'-Hexahydroxy-5,5'-diisopropyl-3,3'-dimethyl-[2,2']binaphthyl-8,8'-dicarbaldehyde bis-ethylimine. The reaction occurs with solvents diethyl ether, propan-2-ol at temperature of 20-45 °C. The yield is 96 %.
When you are dealing with this chemical, you should be very careful. This chemical is inflammation to the skin, eyes and respiratory system or other mucous membranes. If swallowed, it's harmful to health. It may cause damage to health. Therefore, you should wear suitable protective clothing, gloves and eye/face protection. And you must take off immediately all contaminated clothing. In case of contacting with eyes, you should rinse immediately with plenty of water and seek medical advice.
You can still convert the following datas into molecular structure:
(1) SMILES: Cc1cc2c(c(c(c(c2C(C)C)O)O)C=O)c(c1c3c(cc4c(c3O)c(c(c(c4C(C)C)O)O)C=O)C)O
(2) 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
(3) InChIKey: QBKSWRVVCFFDOT-UHFFFAOYSA-N
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
pig | LD50 | oral | 550mg/kg (550mg/kg) | BEHAVIORAL: MUSCLE WEAKNESS GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" | Journal of the American Oil Chemists' Society. Vol. 40, Pg. 571, 1963. |
rat | LD50 | oral | 2315mg/kg (2315mg/kg) | Journal of the American Oil Chemists' Society. Vol. 37, Pg. 40, 1960. |