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| CAS No.: | 302-79-4 |
|---|---|
| Name: | Tretinoin |
| Article Data: | 98 |
| Molecular Structure: | |
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| Formula: | C20H28O2 |
| Molecular Weight: | 300.441 |
| Synonyms: | (2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraenoate;all-trans-beta-Retinoic acid;Vitamin A acid;Tretinoine (French) (EINECS);Retin A;trans-Retinoic acid;all-trans-Vitamin A1 acid;Acide retinoique (French) (DSL);2,4, 6,8-Nonatetranoic acid, 3,7-dimethyl-9-(2,6, 6-trimethyl-1-cyclohexen-1-yl)-, (2E, 4E, 6E, 8E)-;all-trans-Retinoate;AGN 100335;Vitamin A acid sodium salt;Vitamin A1 acid, all-trans-;ATRA;Retin-A;Vesnaroid;Tretin M;all-(E)-Retinoic acid;Retinoic acid, sodium salt;beta-Retinoic acid;Cordes Vas;Aberel;Tretinoin, all-trans-;Retionic acid;Dermairol;Eudyna;Aknefug;Retinoate;all-trans-Retinoic acid;Retacnyl;Tretinoin (all-trans retinoic acid );Tretinoin USP26; |
| EINECS: | 206-129-0 |
| Density: | 1.011 g/cm3 |
| Melting Point: | 179-184 °C |
| Boiling Point: | 462.8 °C at 760 mmHg |
| Flash Point: | 350.6 °C |
| Solubility: | insoluble in water |
| Appearance: | yellow-orange powder |
| Hazard Symbols: |
 T, Xn
|
| Risk Codes: | 22-63-38-20/21/22 |
| Safety: | 53-26-36/37/39-45-36/37 |
| PSA: | 37.30000 |
| LogP: | 5.60260 |
| Conditions | Yield |
|---|---|
| With sodium hydroxide In methanol at 50℃; for 0.5h; | 98% |
| With potassium hydroxide In ethanol | 83% |
| With potassium hydroxide In ethanol at 50℃; | 83% |
| With potassium hydroxide In ethanol for 0.166667h; Heating; | 71% |
| Conditions | Yield |
|---|---|
| With tris(triphenylphosphine)ruthenium(II) chloride; oxygen; bis-(3-methyl-1-imidazolyl)ethylene tetrafluoroborate In hexane at 50℃; under 760.051 Torr; for 3h; Reagent/catalyst; Darkness; | 90.2% |
| Multi-step reaction with 2 steps 1: MnO2 / CH2Cl2 / 2 h / Ambient temperature 2: 80 percent / AgO, NaCN / methanol / 18 h / Ambient temperature View Scheme | |
| Multi-step reaction with 2 steps 1: 90 percent / MnO2 / CH2Cl2 / Ambient temperature 2: AgO / CNNa / methanol View Scheme |
(6R,7R)-3-[(2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraenoyloxymethyl]-5,8-dioxo-7-(2-phenoxy-acetylamino)-5λ4-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid
A
all-trans-retinoic-acid
| Conditions | Yield |
|---|---|
| With β-lactamase from Staphylococcus aureus 95; deuterated phosphate buffer In dimethylsulfoxide-d6 at 25℃; pH=7.2; | A n/a B 86% |
trans-β-formyl crotonic acid
all-trans-retinoic-acid
| Conditions | Yield |
|---|---|
| Stage #1: trans-β-formyl crotonic acid; [3-methyl-5-(2,6,6-trimethylcyclohexene-1-yl)-2E,4E-pentadiene]-triphenyl phosphonic chloride With potassium hydroxide In isopropyl alcohol at -5 - 0℃; for 2h; Wittig Olefination; Inert atmosphere; Stage #2: With hydrogenchloride; palladium diacetate In isopropyl alcohol at 50℃; pH=7 - 8; pH-value; Reagent/catalyst; Temperature; | 85.3% |
trans-β-formyl crotonic acid
[(2E,4E)-3-methyl-5-(2,6,6-trimethylcyclohex-1-en-1-yl)penta-2,4-dienyl]triphenylphosphonium chloride
all-trans-retinoic-acid
| Conditions | Yield |
|---|---|
| Stage #1: trans-β-formyl crotonic acid; [(2E,4E)-3-methyl-5-(2,6,6-trimethylcyclohex-1-en-1-yl)penta-2,4-dienyl]triphenylphosphonium chloride With potassium hydroxide In isopropyl alcohol at -5 - 0℃; for 2h; Wittig Olefination; Inert atmosphere; Stage #2: With hydrogenchloride; palladium diacetate In isopropyl alcohol at 50℃; pH=7-8; Reagent/catalyst; Temperature; pH-value; Inert atmosphere; | 85.3% |
| Conditions | Yield |
|---|---|
| With silver(II) oxide; sodium cyanide In methanol for 18h; Ambient temperature; | 80% |
| With sodium cyanide; silver(l) oxide | 80% |
| With silver(II) oxide; sodium cyanide In methanol Yield given; |
| Conditions | Yield |
|---|---|
| With potassium hydroxide In ethanol for 0.5h; Heating; Yield given; | A n/a B 77% |
| With potassium hydroxide In ethanol for 0.5h; Heating; Yields of byproduct given; | A n/a B 77% |
(2E,4E)-5-iodo-3-methylpenta-2,4-dienoic acid
all-trans-retinoic-acid
| Conditions | Yield |
|---|---|
| [PdCl2(NCMe)2] In N,N-dimethyl-formamide at 25℃; for 3h; Stille cross-coupling reaction; | 73% |
acide-2-carboxy-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2E,4E,6E,8E-tetraenoique
all-trans-retinoic-acid
| Conditions | Yield |
|---|---|
| With pyridine In dichloromethane | 67% |
5-(2,6,6-trimethyl-cyclohex-1-enyl)-3-methyl-1-phenyl-sulphonyl-penta-2,4-diene
(E)-4-bromo-3-methyl-2-butenoic acid
all-trans-retinoic-acid
| Conditions | Yield |
|---|---|
| Stage #1: 5-(2,6,6-trimethyl-cyclohex-1-enyl)-3-methyl-1-phenyl-sulphonyl-penta-2,4-diene With potassium tert-butylate In tetrahydrofuran at -20℃; for 0.5h; Stage #2: (E)-4-bromo-3-methyl-2-butenoic acid In tetrahydrofuran at -20 - 60℃; for 4h; Julia olefination; | 65% |
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Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.
The Tretinoin, with the CAS registry number 302-79-4,is also known as 3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic acid; all-trans-Retinoic acid; Vitamin A acid. It belongs to the product categories of Intermediates & Fine Chemicals;Retinoids;Intracellular receptor;API.Its EINECS number is 206-129-0. This chemical's molecular formula is C20H28O2 and molecular weight is 300.44. What's more,Its systematic name is Tretinoin.It is a yellow-orange powder which has been used to treat acne and other skin problems, and can be used for the unusual type of acne, psoriasis ichthyosis and abnormal.
Physical properties about Tretinoin are:
(1)ACD/LogP: 6.83; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 5.99; (4)ACD/LogD (pH 7.4): 4.19; (5)ACD/BCF (pH 5.5): 13226.03; (6)ACD/BCF (pH 7.4): 210.25; (7)ACD/KOC (pH 5.5): 17912.95; (8)ACD/KOC (pH 7.4): 284.76; (9)#H bond acceptors: 2; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 5; (12)Index of Refraction: 1.556; (13)Molar Refractivity: 95.527 cm3; (14)Molar Volume: 297.151 cm3; (15)Surface Tension: 39.1399993896484 dyne/cm; (16)Density: 1.011 g/cm3; (17)Flash Point: 350.596 °C; (18)Enthalpy of Vaporization: 79.324 kJ/mol; (19)Boiling Point: 462.801 °C at 760 mmHg; (20)Vapour Pressure: 0 mmHg at 25°C.3. Structure Descriptors of Tretinoin
You can still convert the following datas into molecular structure:
(1)SMILES:O=C(O)\C=C(\C=C\C=C(\C=C\C1=C(\CCCC1(C)C)C)C)C;
(2)Std. InChI:InChI=1S/C20H28O2/c1-15(8-6-9-16(2)14-19(21)22)11-12-18-17(3)10-7-13-20(18,4)5/h6,8-9,11-12,14H,7,10,13H2,1-5H3,(H,21,22)/b9-6+,12-11+,15-8+,16-14+;
(3)Std. InChIKey:SHGAZHPCJJPHSC-YCNIQYBTSA-N.
Safety Information of Tretinoin:
The Tretinoin is harmful by inhalation, in contact with skin and if swallowed and rritating to skin. It is possible risk of harm to the unborn child. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) .When you use it wear suitable protective clothing, gloves and eye/face protection. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. This chemical is danger to the environment Avoid exposure - obtain special instructions before use.
Toxicity of Tretinoin is as follows:
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| mouse | LD50 | intraperitoneal | 208mg/kg (208mg/kg) | Drugs in Japan Vol. -, Pg. 886, 1995. | |
| mouse | LD50 | intravenous | 92mg/kg (92mg/kg) | United States Patent Document. Vol. #3878202, | |
| mouse | LD50 | oral | 1100mg/kg (1100mg/kg) | American Journal of Clinical Nutrition. Vol. 52, Pg. 183, 1990. | |
| mouse | LD50 | subcutaneous | 253mg/kg (253mg/kg) | BEHAVIORAL: SLEEP LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION | Kiso to Rinsho. Clinical Report. Vol. 7, Pg. 3194, 1973. |
| rat | LD50 | intraperitoneal | 96mg/kg (96mg/kg) | SPINAL CORD: OTHER DEGENERATIVE CHANGES BEHAVIORAL: ATAXIA BLOOD: NORMOCYTIC ANEMIA | Kiso to Rinsho. Clinical Report. Vol. 7, Pg. 3194, 1973. |
| rat | LD50 | intravenous | 75mg/kg (75mg/kg) | Drugs in Japan Vol. -, Pg. 886, 1995. | |
| rat | LD50 | oral | 2gm/kg (2000mg/kg) | American Journal of Clinical Nutrition. Vol. 52, Pg. 183, 1990. | |
| rat | LD50 | subcutaneous | 53mg/kg (53mg/kg) | BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS" LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION | Kiso to Rinsho. Clinical Report. Vol. 7, Pg. 3194, 1973. |
