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| CAS No.: | 4759-48-2 |
|---|---|
| Name: | Isotretinoin |
| Molecular Structure: | |
|
|
|
| Formula: | C20H28O2 |
| Molecular Weight: | 300.441 |
| Synonyms: | Isotretinoin [USAN:BAN:INN];(2Z,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraenoate;Retinoic acid, (13cis)-;13-cis-Retinoic acid;Isotretinoin Retinoic acid;Prestwick_642;Neovitamin A acid;Claravis;Teriosal;Roaccutan;Isotretion;Isotretinoin?;Isotretinoine [INN-French];isoretinoin;4-09-00-02388 (Beilstein Handbook Reference); |
| EINECS: | 225-296-0 |
| Density: | 1.011 g/cm3 |
| Melting Point: | 172-175 °C(lit.) |
| Boiling Point: | 462.8 °C at 760 mmHg |
| Flash Point: | 350.6 °C |
| Solubility: | insoluble in water |
| Appearance: | yellowish crystalline powder |
| Hazard Symbols: |
 T
|
| Risk Codes: | 61-36/37/38-20/21/22 |
| Safety: | 53-26-36/37/39-45 |
| PSA: | 37.30000 |
| LogP: | 5.60260 |
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- 99170-93-1N-Methyl-2-oxazolamine
- 20013-34-7
acide-2-carboxy-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2E,4E,6E,8E-tetraenoique
- 4759-48-2
13-cis-retinoic acid
| Conditions | Yield |
|---|---|
| With 2,6-dimethylpyridine for 2h; Heating; | 90% |
| With lutidine Heating; | 63% |
| With 2,6-dimethylpyridine for 1.5h; Decarboxylation; | 56% |
| With 2,6-dimethylpyridine for 0.3h; Heating; |
- 70143-04-3
(Z)-3-methyl-4-oxobut-2-enoic acid
- 62285-98-7
5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide
- 4759-48-2
13-cis-retinoic acid
| Conditions | Yield |
|---|---|
| Stage #1: (Z)-3-methyl-4-oxobut-2-enoic acid; 5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide With sodium hydroxide In isopropyl alcohol at 20 - 30℃; for 3h; Wittig Olefination; Inert atmosphere; Stage #2: With hydrogenchloride; palladium diacetate In isopropyl alcohol at 60℃; pH=7 - 8; | 86.3% |
| Stage #1: (Z)-3-methyl-4-oxobut-2-enoic acid; 5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide With sodium hydroxide In isopropyl alcohol at 20 - 30℃; for 3h; Wittig Olefination; Inert atmosphere; Stage #2: With hydrogenchloride; palladium diacetate In isopropyl alcohol at 60℃; pH=7-8; Inert atmosphere; | 86.3% |
- 43059-50-3
4-methyl-6-[(1E,3E)-2-methyl-4-(2,6,6-trimethylcyclohex-1-en-1-yl)buta-1,3-dien-1-yl]-5,6-dihydro-2H-pyran-2-one
- 4759-48-2
13-cis-retinoic acid
| Conditions | Yield |
|---|---|
| With potassium tert-butylate In tetrahydrofuran at 0℃; for 1h; | 80% |
| With pyrographite for 0.5h; Reflux; | 55 g |
| 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% |
- 59699-82-0
13-cis-ethyl retinoate
- 4759-48-2
13-cis-retinoic acid
| Conditions | Yield |
|---|---|
| With sodium hydroxide In ethanol at 50℃; | 70% |
| With sodium hydroxide |
- 220212-07-7
(2Z,4E)-5-iodo-3-methylpenta-2,4-dienoic acid
- 4759-48-2
13-cis-retinoic acid
| Conditions | Yield |
|---|---|
| [PdCl2(NCMe)2] In N,N-dimethyl-formamide at 25℃; for 3h; Stille cross-coupling reaction; | 70% |
- 81176-73-0
11-cis,13-cis-12-carboxyretinoic acid
- 4759-48-2
13-cis-retinoic acid
| Conditions | Yield |
|---|---|
| With copper (I) acetate In various solvent(s) at 110℃; for 2.5h; | 68.2% |
| With 2,4-lutidine; copper diacetate |
- 105593-28-0
β-ionone
- 75-16-1
methylmagnesium bromide
- 419550-09-7
dimethyl 2-[(2E)-3-(dimethylamino)-1-methyl-2-propenylidene]malonate
A
- 4759-48-2
13-cis-retinoic acid
B
- 302-79-4
all-trans-retinoic-acid
| Conditions | Yield |
|---|---|
| Multistep reaction.; | A 12% B 61% |
- 20013-34-7
acide-2-carboxy-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2E,4E,6E,8E-tetraenoique
A
- 4759-48-2
13-cis-retinoic acid
B
- 302-79-4
all-trans-retinoic-acid
| Conditions | Yield |
|---|---|
| With pyridine In dichloromethane at 20℃; for 20h; | A n/a B 60% |
| With barium dihydroxide In benzene for 0.5h; |
- 81176-73-0
11-cis,13-cis-12-carboxyretinoic acid
A
- 4759-48-2
13-cis-retinoic acid
B
- 70244-78-9, 94440-28-5
2-((1E,3E,5E)-3,7-dimethylocta-1,3,5,7-tetraen-1-yl)-1,3,3-trimethylcyclohex-1-ene
| Conditions | Yield |
|---|---|
| With copper (I) acetate In pyridine at 100℃; for 2h; Product distribution; other solvents, other temperatures, other times; | A 49.8% B 33.9% |
| With copper (I) acetate In pyridine at 100℃; for 3h; | A 45.6% B 30.8% |
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Chemistry
IUPAC Name: (2Z,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoic acid
Synonyms of 13-cis-Vitamin A acid (CAS NO.4759-48-2): 13-cis-Vitamin A acid;3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)2-cis-4-trans-6-trans-8-trans-nonatetraenoic acid ; Accutane ; Isotretinoin ; Isotretinoinum ; Neovitamin A acid
CAS NO: 4759-48-2
Molecular Formula: C20H28O2
Molecular Weight: 300.44
Molecular Structure: 
EINECS: 225-296-0
Melting Point: 172-175 °C(lit.)
Storage temp: -20°C
Index of Refraction: 1.556
Molar Refractivity: 95.52 cm3
Molar Volume: 297.1 cm3
Surface Tension: 39.1 dyne/cm
Density: 1.011 g/cm3
Flash Point: 350.6°C
Boiling Point: 462.8 °C at 760 mmHg
Enthalpy of Vaporization: 79.32 kJ/mol
Water Solubility: insoluble
Appearance: Yellow-Orange Crystalline Powder
Stability: Stable, but probably air and light sensitive. Combustible. Incompatible with strong oxidizing agents.
Product Categories of 13-cis-Vitamin A acid (CAS NO.4759-48-2): Antibiotics;Organic acids;APIs;Intermediates & Fine Chemicals;Pharmaceuticals;Retinoids
SMILES: O=C(O)C=C(C=CC=C(C=C/C1=C(/CCCC1(C)C)C)C)C
InChI: InChI=1/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)
InChIKey: SHGAZHPCJJPHSC-UHFFFAOYAP
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)
Std. InChIKey: SHGAZHPCJJPHSC-UHFFFAOYSA-N
Uses
13-cis-Vitamin A acid (CAS NO.4759-48-2) is used as a treatment for severe acne. Presently being studied in conjuction with the treatment of photoaged skin. It is a topical keratolytic agent which is used in the treatment skin diseases including acne vulgaris. It inhibits the secretion of sebum and alters the lipid composition of the skin surface. Besides, it also shows antiinflammatory and antitumor activities by gene regulation.
Toxicity Data With Reference
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| child | TDLo | oral | 30mg/kg/21W (30mg/kg) | MUSCULOSKELETAL: OTHER CHANGES SKIN AND APPENDAGES (SKIN): "DERMATITIS, IRRITATIVE: AFTER SYSTEMIC EXPOSURE" SKIN AND APPENDAGES (SKIN): NAILS: OTHER | American Journal of Diseases of Children. Vol. 142, Pg. 316, 1988. |
| child | TDLo | oral | 360mg/kg/26W- (360mg/kg) | SKIN AND APPENDAGES (SKIN): SWEATING: OTHER | CUTIS; Cutaneous Medicine for the Practitioner. Vol. 38, Pg. 275, 1986. |
| man | TDLo | oral | 24mg/kg/4W-I (24mg/kg) | GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" GASTROINTESTINAL: OTHER CHANGES | Gastroenterology. Vol. 93, Pg. 606, 1987. |
| man | TDLo | oral | 37mg/kg/5W-I (37mg/kg) | SKIN AND APPENDAGES (SKIN): "DERMATITIS, IRRITATIVE: AFTER SYSTEMIC EXPOSURE" IMMUNOLOGICAL INCLUDING ALLERGIC: DECREASED IMMUNE RESPONSE | Archives of Dermatology. Vol. 122, Pg. 815, 1986. |
| man | TDLo | unreported | 21mg/kg/3W-I (21mg/kg) | SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" | British Medical Journal. Vol. 290, Pg. 820, 1985. |
| mouse | LD50 | intraperitoneal | 138mg/kg (138mg/kg) | "The Retinoids, Vol.2," Sporn, M.B., et al., eds., New York, Academic Press, Inc., 1984Vol. 2, Pg. 287, 1984. | |
| mouse | LD50 | oral | 3389mg/kg (3389mg/kg) | "The Retinoids, Vol.2," Sporn, M.B., et al., eds., New York, Academic Press, Inc., 1984Vol. 2, Pg. 287, 1984. | |
| rabbit | LD50 | oral | 1960mg/kg (1960mg/kg) | "The Retinoids, Vol.2," Sporn, M.B., et al., eds., New York, Academic Press, Inc., 1984Vol. 2, Pg. 287, 1984. | |
| rat | LD50 | intraperitoneal | 901mg/kg (901mg/kg) | Journal of the American Academy of Dermatology. Vol. 6, Pg. 652, 1982. | |
| rat | LD50 | oral | > 4gm/kg (4000mg/kg) | Journal of the American Academy of Dermatology. Vol. 6, Pg. 652, 1982. | |
| women | TDLo | oral | 56mg/kg/8W-I (56mg/kg) | SKIN AND APPENDAGES (SKIN): "DERMATITIS, IRRITATIVE: AFTER SYSTEMIC EXPOSURE" | CUTIS; Cutaneous Medicine for the Practitioner. Vol. 37, Pg. 115, 1986. |
Consensus Reports
Reported in EPA TSCA Inventory.
Safety Profile
Hazard Codes: 
T
Risk Codes: 61-36/37/38-20/21/22
R61:May cause harm to the unborn child.
R20/21/22: Harmful by inhalation, in contact with skin and if swallowed.
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Codes: 53-26-36/37/39-45
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical
advice.
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection.
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the
label whenever possible.)
S53: Avoid exposure - obtain special instructions before use.
WGK Germany: 3
RTECS: VH6440000
Poison by intraperitoneal route. Moderately toxic by ingestion. A human teratogen by ingestion with fetal developmental abnormalities of the skin and appendages and other postnatal effects. Human reproductive effects. Human systemic effects: decreased immune response, diarrhea, hypermotility, irritative dermatitis, sweating. Human mutation data reported. An experimental teratogen. Other experimental reproductive effects. When heated to decomposition it emits acrid smoke and irritating fumes.
Specification
General Information: As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear.
Extinguishing Media: Use water spray, dry chemical, carbon dioxide, or chemical foam.
Handling: Do not breathe dust, vapor, mist, or gas. Do not get in eyes, on skin, or on clothing. Use only in a chemical fume hood.
Storage: Do not store in direct sunlight. Store in a tightly closed container. Store in a dry area. Store in freezer.