Isotretinoin supplier | CasNO.4759-48-2

Name
Isotretinoin
EINECS 225-296-0
CAS No. 4759-48-2
Article Data68
CAS DataBase
Density 1.011 g/cm³
Solubility insoluble in water
Melting Point 172-175 °C(lit.)
Formula C₂₀H₂₈O₂
Boiling Point 462.8 °C at 760 mmHg
Molecular Weight 300.441
Flash Point 350.6 °C
Transport Information
Appearance yellowish crystalline powder
Safety 53-26-36/37/39-45
Risk Codes 61-36/37/38-20/21/22
Molecular Structure
Hazard Symbols T
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);
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%

: 87424-83-7
4-Methyl-6-<(1E,3E)-2-methyl-4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-1,3-butadien-1-yl>-2H-pyran-2-on

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

Conditions

Conditions	Yield
With potassium hydroxide; sodium tetrahydroborate In methanol for 6h; Heating;	42%

: 1620084-74-3
(2E,4E,6E,8E)-3,7-dimethyl-9-{6,6-dimethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolanyl)-1-cyclohexenyl}-2,4,6,8-nonatetraenoicacid ethyl ester

: 74-88-4
methyl iodide

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

B: 302-79-4, 3555-80-4, 4759-48-2, 5300-03-8, 5352-74-9, 68070-34-8, 68070-35-9, 97950-17-9, 98462-64-7, 124510-04-9
9-cis-retinoic acid

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

Conditions

Conditions	Yield
Stage #1: (2E,4E,6E,8E)-3,7-dimethyl-9-{6,6-dimethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolanyl)-1-cyclohexenyl}-2,4,6,8-nonatetraenoicacid ethyl ester; methyl iodide With tris-(dibenzylideneacetone)dipalladium(0); potassium carbonate; tris-(o-tolyl)phosphine In water; N,N-dimethyl-formamide at 60℃; for 0.0833333h; Inert atmosphere; Schlenk technique; Stage #2: With potassium hydroxide In methanol; water; N,N-dimethyl-formamide at 100℃; for 0.0333333h; Inert atmosphere; Schlenk technique; Stage #3: With formic acid In methanol; water; N,N-dimethyl-formamide Inert atmosphere; Schlenk technique;	A 10% B 0.5% C 32%

Yield

Stage #1: (2E,4E,6E,8E)-3,7-dimethyl-9-{6,6-dimethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolanyl)-1-cyclohexenyl}-2,4,6,8-nonatetraenoicacid ethyl ester; methyl iodide With tris-(dibenzylideneacetone)dipalladium(0); potassium carbonate; tris-(o-tolyl)phosphine In water; N,N-dimethyl-formamide at 60℃; for 0.0833333h; Inert atmosphere; Schlenk technique;
Stage #2: With potassium hydroxide In methanol; water; N,N-dimethyl-formamide at 100℃; for 0.0333333h; Inert atmosphere; Schlenk technique;
Stage #3: With formic acid In methanol; water; N,N-dimethyl-formamide Inert atmosphere; Schlenk technique;

A 10%
B 0.5%
C 32%

...Expand

: 638-10-8
ethyl 3-methylbut-2-enoate

: 3917-41-7
(2E,4E)-3-methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadienal

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

Conditions

Conditions	Yield
With sodium amide

: 41551-56-8, 78088-24-1, 78088-25-2, 78088-26-3
methyl 5-benzenesulphonyl-3.7-dimethyl-9-(2'.6'.6'.trimethyl-cyclohexen-1'-yl)-2.6.8-nonatrienoate

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

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

Conditions

Conditions	Yield
With potassium hydroxide In methanol for 2.5h; Heating; Yield given. Yields of byproduct given;

: 146558-55-6
8-<2-(methylthio)-1,3-dithian-2-yl>-3,7-dimethyl-1-(2,6,6-trimethylcyclohex-1-enyl)octa-1E,3E,5E,7E-tetraene

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

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

Conditions

Conditions	Yield
Yield given. Multistep reaction. Yields of byproduct given;

: 16760-45-5
(2Z,4E,6E,8E)-methyl 3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoate

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

Conditions

Conditions	Yield
With potassium hydroxide In methanol at 50℃; for 2h;

: 73395-75-2
(E)-2-(but-1-en-3-ynyl)-1,3,3-trimethylcyclohex-1-ene

: 220212-07-7
(2Z,4E)-5-iodo-3-methylpenta-2,4-dienoic acid

: 74-88-4
methyl iodide

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

Conditions

Conditions	Yield
Yield given. Multistep reaction;

...Expand

: 472-86-6
13-cis-vitamin A aldehyde

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

B: 71423-68-2
4-hydroxy-13-cis-retinal

Conditions

Conditions	Yield
With rabbit liver microsomal P450 1A1 isozyme; NADPH; NADPH-cytochrome P450 reductase In phosphate buffer at 30℃; for 0.25h; pH=7.4; Enzyme kinetics; Further Variations:; Reaction partners; Oxidation; Enzymatic reaction;

: 472-86-6
13-cis-vitamin A aldehyde

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

Conditions

Conditions	Yield
With cytosolic aldehyde dehydrogenase from human liver In phosphate buffer; dimethyl sulfoxide at 25℃; for 1h; pH=7.5; Enzyme kinetics;
Multi-step reaction with 2 steps 1: 60 percent / NaCN, AgO, MnO2 / 14 h / 40 °C 2: 70 percent / 6 M NaOH / ethanol / 50 °C View Scheme
Multi-step reaction with 2 steps 1: AgO, MnO2, NaCN 2: NaOH View Scheme

: 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

C: 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 triethylamine In benzene for 0.3h; Heating;

...Expand

: methyl 14-(methoxycarbonyl)-retro-retionate

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

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

Conditions

Conditions	Yield
With potassium hydroxide In ethanol; water at 40℃; for 0.75h;	A 1.05 g B 5 g

: 924-59-4
diethyl 3-methylpent-2-enedioate

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

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 85 percent / potassium hydroxide / methanol / 64 h / 20 °C 2: 49.8 percent / copper acetate / pyridine; various solvent(s) / 2 h / 100 °C / other solvents, other temperatures, other times View Scheme
Multi-step reaction with 2 steps 1: 85 percent / potassium hydroxide / methanol / 64 h / 20 °C 2: 68.2 percent / copper acetate / various solvent(s) / 2.5 h / 110 °C View Scheme

: 3917-41-7
(2E,4E)-3-methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadienal

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

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 85 percent / potassium hydroxide / methanol / 64 h / 20 °C 2: 49.8 percent / copper acetate / pyridine; various solvent(s) / 2 h / 100 °C / other solvents, other temperatures, other times View Scheme
Multi-step reaction with 2 steps 1: 85 percent / potassium hydroxide / methanol / 64 h / 20 °C 2: 68.2 percent / copper acetate / various solvent(s) / 2.5 h / 110 °C View Scheme
Multi-step reaction with 3 steps 1: MeOK 2: KOH / methanol; H2O 3: 2,6-dimethylpiridine / 0.3 h / Heating View Scheme

: 13830-91-6
diethyl bromoisopropylidenemalonate

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

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C 1.2: 74 percent / tetrahydrofuran; hexane / 1.5 h / -78 - 20 °C 2.1: 58 percent / KOH / propan-2-ol / 27 h / 20 °C 3.1: 63 percent / lutidine / Heating View Scheme

: 38987-91-6
5-(2,6,6-trimethyl-cyclohex-1-enyl)-3-methyl-1-phenyl-sulphonyl-penta-2,4-diene

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

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C 1.2: 74 percent / tetrahydrofuran; hexane / 1.5 h / -78 - 20 °C 2.1: 58 percent / KOH / propan-2-ol / 27 h / 20 °C 3.1: 63 percent / lutidine / Heating View Scheme
Multi-step reaction with 2 steps 1: potassium t-butoxide / tetrahydrofuran; various solvent(s) / 1 h / -65 °C 2: potassium hydroxide / methanol / 2.5 h / Heating View Scheme

: 777916-02-6
2-[(4E,6E)-3-Benzenesulfonyl-1,5-dimethyl-7-(2,6,6-trimethyl-cyclohex-1-enyl)-hepta-4,6-dienylidene]-malonic acid diethyl ester

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

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 58 percent / KOH / propan-2-ol / 27 h / 20 °C 2: 63 percent / lutidine / Heating View Scheme

: 22035-53-6
dimethyl isopropylidenemalonate

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

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 95 percent / methanol / 18 h / 95 °C 2: 65 percent / iPr2NH / 1,2-dimethoxy-ethane; hexane / 2 h / Heating 3: 69 percent / tetrahydrofuran / 0.5 h / -10 °C 4: 1.05 g / KOH / ethanol; H2O / 0.75 h / 40 °C View Scheme
Multi-step reaction with 3 steps 1: MeOK 2: KOH / methanol; H2O 3: 2,6-dimethylpiridine / 0.3 h / Heating View Scheme
Multi-step reaction with 3 steps 1: MeOK 2: KOH / methanol; H2O 3: Ba(OH)2 / benzene / 0.5 h View Scheme

: 419550-09-7
dimethyl 2-[(2E)-3-(dimethylamino)-1-methyl-2-propenylidene]malonate

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

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 65 percent / iPr2NH / 1,2-dimethoxy-ethane; hexane / 2 h / Heating 2: 69 percent / tetrahydrofuran / 0.5 h / -10 °C 3: 1.05 g / KOH / ethanol; H2O / 0.75 h / 40 °C View Scheme

: 419550-36-0
dimethyl 2-[(3E,6E)-1-methyl-5-oxo-7-(2,6,6-trimethyl-1-cyclohexen-1-yl)-1,3,6-heptatrienyl]malonate

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

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 69 percent / tetrahydrofuran / 0.5 h / -10 °C 2: 1.05 g / KOH / ethanol; H2O / 0.75 h / 40 °C View Scheme

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

: 18107-18-1
diazomethyl-trimethyl-silane

: 16760-45-5
(2Z,4E,6E,8E)-methyl 3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoate

Conditions

Conditions	Yield
In methanol; hexane; benzene	83%
In methanol; hexane; benzene	83%
In methanol; hexane; benzene at 20℃; for 0.75h;

: 36653-82-4
1-Hexadecanol

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

: 847550-90-7
C36H60O2

Conditions

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0℃; for 24h; optical yield given as %de;	81%

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

: 53839-60-4
retinoyl chloride

: 138752-02-0
all-(E)-retinoic and 13-(Z)-retinoic anhydride

Conditions

Conditions	Yield
With triethylamine In benzene for 0.5h; Ambient temperature;	76.7%

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

: 64291-41-4
(2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(4-(hydroxymethyl)phenoxy)-tetrahydro-2H-pyran-3,4,5-triyl triacetate

: 3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraenoic acid 4-(3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-benzyl ester

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃;	74%

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

: 4064-06-6
1,2:3,4-di-O-isopropylidene-α-D-galactopyranose

: 6-O-13-cis-retinoyl-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 10h;	73.2%

: 504-24-5
4-aminopyridine

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

: (13cis)-15-(pyridin-4-ylamino)retinal

Conditions

Conditions	Yield
With dicyclohexyl-carbodiimide In dichloromethane for 5h;	70%

: 929016-73-9
acetic acid 4,5-diacetoxy-6-acetoxymethyl-2-(5-hydroxymethyl-2-methoxy-phenoxy)-tetrahydro-pyran-3-yl ester

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

: 929016-74-0
3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraenoic acid 4-methoxy-3-(3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-benzyl ester

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 10h;	67.1%

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

: 141-43-5
ethanolamine

: 75686-05-4
13-cis-N-(2-Hydroxyethyl)retinamide

Conditions

Conditions	Yield
With 1,1'-carbonyldiimidazole In benzene 1.) 20-25 deg C, 3 h, 50 deg C, 15 min, 2.) 10-20 deg C, 2 h;	66%

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

: 3068-31-3
1-bromo-2,3,4-tri-O-acetyl-α-D-xylopyranose

: 1-O-13-cis-retinoyl-2,3,4-tri-O-acetyl-β-D-xylopyranose

Conditions

Conditions	Yield
With dmap; potassium hydroxide In dichloromethane for 9h; Heating;	65%

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

: 572-09-8
2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

: 1-O-13-cis-retinoyl-2,3,4,6-tetra-O-acetyl-β-D-glucopyranose

Conditions

Conditions	Yield
With dmap; potassium hydroxide In dichloromethane for 6h; Heating;	61.4%

: 13325-10-5
4-Aminobutanol

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

: 84680-31-9
13-cis-N-(4-Hydroxybutyl)retinamide

Conditions

Conditions	Yield
With 1,1'-carbonyldiimidazole In benzene 1.) 20-25 deg C, 3 h, 50 deg C, 15 min, 2.) 10-20 deg C, 2 h;	60%

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

: 4753-07-5
2,3,6,2',3',4',6'-hepta-O-acetyl-lactosyl bromide

: 1-O-13-cis-retinoyl-2,3,6,2',3',4',6'-hepta-O-acetyl-β-lactose

Conditions

Conditions	Yield
With dmap; potassium hydroxide In dichloromethane for 9h; Heating;	55.6%

: 929016-65-9
[2-(hydroxymethyl)phenyl]-2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside

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

: 3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraenoic acid 2-(3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-benzyl ester

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 10h;	55.4%

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

: 2196-99-8
2-chloro-1-(4-methoxyphenyl)ethanone

: 2-(13-cis-retinoyloxy)-4'-methoxyacetophenone

Conditions

Conditions	Yield
With caesium carbonate In N-methyl-acetamide; water	54%

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

: 4753-07-5, 5160-10-1, 14206-57-6, 14227-66-8, 14257-35-3, 42385-75-1, 67650-37-7, 68682-05-3, 69308-57-2, 69349-74-2, 70223-96-0, 70223-97-1, 71276-38-5, 85248-99-3, 118493-15-5, 120575-76-0
2,3,6,2',3',4',6'-hepta-O-acetyl-α-D-maltosyl bromide

: 1-O-13-cis-retinoyl-2,3,6,2',3',4',6'-hepta-O-acetyl-β-maltose

Conditions

Conditions	Yield
With dmap; potassium hydroxide In dichloromethane for 9h; Heating;	53.1%

: L-cysteic acid monohydrate

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

: N-(13-cis-retinoyl)-L-cysteic acid (Sodium Salt)

Conditions

Conditions	Yield
	35%

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

: 14857-77-3
L-homocysteic acid

: N-(13-cis-retinoyl)-L-homocysteic Acid (Sodium Salt)

Conditions

Conditions	Yield
	25%

Isotretinoin Chemical Properties

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

Isotretinoin 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.

Isotretinoin 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.

Isotretinoin Consensus Reports

Reported in EPA TSCA Inventory.

Isotretinoin 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.

Isotretinoin 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.

Product Name

Isotretinoin

Synthetic route

Isotretinoin Chemical Properties

Isotretinoin Uses

Isotretinoin Toxicity Data With Reference

Isotretinoin Consensus Reports

Isotretinoin Safety Profile

Isotretinoin Specification

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