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4759-48-2

Basic Information
CAS No.: 4759-48-2
Name: 13-cis-Vitamin A acid
Article Data: 68
Cas Database
Molecular Structure:
Molecular Structure of 4759-48-2 (13-cis-Vitamin A acid)
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: ToxicT
Risk Codes: 61-36/37/38-20/21/22
Safety: 53-26-36/37/39-45
Transport Information: N/A
PSA: 37.30000
LogP: 5.60260
Synthetic route
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With potassium tert-butylate In tetrahydrofuran at 0℃; for 1h;80%
With pyrographite for 0.5h; Reflux;55 g
Conditions
ConditionsYield
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
ConditionsYield
With sodium hydroxide In ethanol at 50℃;70%
With sodium hydroxide
220212-07-7

(2Z,4E)-5-iodo-3-methylpenta-2,4-dienoic acid

tributyl[(1E,3E)-2-methyl-4-(2,6,6-trimethylcyclohex-1-enyl)buta-1,3-dienyl]stannane

4759-48-2

13-cis-retinoic acid

Conditions
ConditionsYield
[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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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%
Downstream Products
16760-45-5
110848-62-9
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    CAS: 4759-48-2 Molecular Formula:C20H27O2 Structural Formula: Melting point:174-177℃ Boiling point:462.8°C at 760 mmHg Uses: Dermatologic agent Appearance: yellow powder Storage:Store in cool and dry place, away

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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/cm
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: ToxicT
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.

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