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Basic Information

Molecular Structure:
CAS No.:	4759-48-2
Name:	Isotretinoin
Article Data:	68
Cas Database

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

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

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

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

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran at 0℃; for 1h;	80%
With pyrographite for 0.5h; Reflux;	55 g

: 3899-20-5, 51249-34-4, 59699-82-0, 85354-08-1, 86708-67-0, 86708-68-1, 86708-69-2, 86708-70-5
ethyl retinoate

A: 4759-48-2
13-cis-retinoic acid

B: 302-79-4
all-trans-retinoic-acid

Conditions

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

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

: 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

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

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

Conditions	Yield
Multistep reaction.;	A 12% B 61%

...Expand

: 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

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

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%

Raw Materials

74-88-4

302-79-4

79-81-2

924-59-4

Downstream Products

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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: Toxic 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.

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