Tretinoin supplier | CasNO.302-79-4

Name
Tretinoin
EINECS 206-129-0
CAS No. 302-79-4
Article Data98
CAS DataBase
Density 1.011 g/cm³
Solubility insoluble in water
Melting Point 179-184 °C
Formula C₂₀H₂₈O₂
Boiling Point 462.8 °C at 760 mmHg
Molecular Weight 300.441
Flash Point 350.6 °C
Transport Information
Appearance yellow-orange powder
Safety 53-26-36/37/39-45-36/37
Risk Codes 22-63-38-20/21/22
Molecular Structure
Hazard Symbols T,Xn
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;
PSA 37.30000
LogP 5.60260

Synthetic route

: 3899-20-5
ethyl (all-E)-retinoate

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

Conditions

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%

: 68-26-8
RETINOL

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

Conditions

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

: 370578-75-9
(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: 302-79-4
all-trans-retinoic-acid

B: (R)-2-[(R)-Carboxy-(2-phenoxy-acetylamino)-methyl]-5-methylene-1-oxo-1,2,5,6-tetrahydro-1λ4-[1,3]thiazine-4-carboxylic acid

Conditions

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%

: 54168-84-2
trans-β-formyl crotonic acid

: [3-methyl-5-(2,6,6-trimethylcyclohexene-1-yl)-2E,4E-pentadiene]-triphenyl phosphonic chloride

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

Conditions

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%

: 54168-84-2
trans-β-formyl crotonic acid

: 53282-28-3
[(2E,4E)-3-methyl-5-(2,6,6-trimethylcyclohex-1-en-1-yl)penta-2,4-dienyl]triphenylphosphonium chloride

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

Conditions

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%

: 116-31-4
all-trans-Retinal

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

Conditions

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;

: 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%

: 220212-06-6
(2E,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

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

Conditions

Conditions	Yield
[PdCl2(NCMe)2] In N,N-dimethyl-formamide at 25℃; for 3h; Stille cross-coupling reaction;	73%

: 20013-34-7
acide-2-carboxy-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2E,4E,6E,8E-tetraenoique

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

Conditions

Conditions	Yield
With pyridine In dichloromethane	67%

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

: 19041-16-8
(E)-4-bromo-3-methyl-2-butenoic acid

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

Conditions

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%

: 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;

aqueous potassium hydroxide: aqueous potassium hydroxide

aqueous sodium chlorite: aqueous sodium chlorite

: 513-35-9
2-methyl-but-2-ene

: 116-31-4
all-trans-Retinal

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

Conditions

Conditions	Yield
With phosphoric acid In 1,4-dioxane; ethanol; hexane	55.9%

...Expand

: [(2Z,4E)-3-methyl-5-(2,6,6-trimethylcyclohex-1-en-1-yl)penta-2,4-dienyl]triphenylphosphonium chloride

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

Conditions

Conditions	Yield
Stage #1: [(2Z,4E)-3-methyl-5-(2,6,6-trimethylcyclohex-1-en-1-yl)penta-2,4-dienyl]triphenylphosphonium chloride With sodium methylate In methanol at -7.5℃; for 1h; Wittig Reaction; Stage #2: With methanol; sodium hydroxide; ethanol; water at 20℃; Heating / reflux; Stage #3: With water; acetic acid In dichloromethane	46%

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

B: 124510-04-9
7-cis-retinoic acid

Conditions

Conditions	Yield
With potassium hydroxide In ethanol; water for 2h; Heating;	A 38% B n/a

: 83802-77-1
retinoyl fluoride

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

Conditions

Conditions	Yield
With water In isopropyl alcohol for 23h;	38%

: 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

: 54168-84-2
trans-β-formyl crotonic acid

: 59057-30-6
(1E)-1-(2,6,6-trimethylcyclohex-1-enyl)-3-methyl-1,4-pentadien-3-ol

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

Conditions

Conditions	Yield
With triphenylphosphine

: 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

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

Conditions

Conditions	Yield
With potassium amide

: 115207-29-9
(+/-)-7-hydroxy-3.7-dimethyl-1t-(2.2.6-trimethyl-cyclohexen-(6)-yl)-nonatrien-(1.3t.5t)-oic acid-(9)-ethyl ester

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

Conditions

Conditions	Yield
With iodine; Petroleum ether Behandeln des erhaltenen all-trans-Retinsaeure-aethylesters mit wss.-aethanol. Kalilauge unter Stickstoff bei Lichtausschluss;

: (+/-)-7-hydroxy-3.7-dimethyl-1t-(2.2.6-trimethyl-cyclohexen-(6)-yl)-nonatrien-(1.3t.5t)-oic acid-(9)-methyl ester

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

Conditions

Conditions	Yield
With oxalic acid unter vermindertem Druck und Behandeln mit methanol. oder aethanol. Kalilauge;
With toluene-4-sulfonic acid; benzene Behandeln mit methanol. oder aethanol. Kalilauge;
With phenyl isocyanate at 110℃; Behandeln mit methanol. oder aethanol. Kalilauge;

: 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
(2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraenoic acid

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

Conditions

Conditions	Yield
With iodine

: 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;

: 131189-98-5, 131235-62-6
(2E,4E,8E/2Z,4E,8E)-7-hydroxy-7-methyl-9-(2,6,6-trimethyl-1-cyclohexenyl)-nona-2,4,8-trienoic acid

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

Conditions

Conditions	Yield
With iodine; toluene-4-sulfonic acid 1.) methylene dichloride, reflux; 2.) diethyl ether/benzene, rt, 7 h; Yield given;
Multi-step reaction with 2 steps 1: 95 percent / p-toluenesulfonic acid / CH2Cl2 / Heating 2: I2 View Scheme

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

: 220212-06-6
(2E,4E)-5-iodo-3-methylpenta-2,4-dienoic acid

: 74-88-4
methyl iodide

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

Conditions

Conditions	Yield
Yield given. Multistep reaction;

...Expand

: 116-31-4
all-trans-Retinal

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

B: 18344-42-8
4-hydroxy-all-trans-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;

: 54168-84-2
trans-β-formyl crotonic acid

3-methyl-5t-<2,6,6-trimethyl-cyclohex-1-enyl>-penta-2t,4-dien-1-ol: 3-methyl-5t-<2,6,6-trimethyl-cyclohex-1-enyl>-penta-2t,4-dien-1-ol

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

Conditions

Conditions	Yield
With triphenylphosphine

4t-<2,6,6-trimethyl-cyclohex-1-enyl>-but-3-en-2-ol: 4t-<2,6,6-trimethyl-cyclohex-1-enyl>-but-3-en-2-ol

3-methyl-6-oxo-hexa-2t,4t-dienoic acid: 3-methyl-6-oxo-hexa-2t,4t-dienoic acid

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

Conditions

Conditions	Yield
With triphenylphosphine

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

: 18107-18-1
diazomethyl-trimethyl-silane

: 339-16-2
all-trans-methyl retinoate

Conditions

Conditions	Yield
In methanol; hexane; benzene at 20℃; for 0.75h;	100%
With methanol In benzene at 20℃; Methylation;

: 36653-82-4
1-Hexadecanol

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

: 136013-95-1
retinyl palmitate

Conditions

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0℃; for 24h; optical yield given as %de;	99%

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

: C20H38O2

Conditions

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; under 760.051 Torr;	99%

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

: 530-62-1
1,1'-carbonyldiimidazole

: 61319-45-7
N-(all-trans-Retinoyl)-imidazole

Conditions

Conditions	Yield
In acetonitrile for 1h; Heating;	98.6%
In N,N-dimethyl-formamide Ambient temperature;	80%
In benzene at 20℃; for 1h;	60%

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

: 131111-38-1
3-(tert-butyldisulfanyl)propane-1,2-diol

: 131111-41-6
(2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraenoic acid 2-tert-butyldisulfanyl-1-[(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraenoyloxymethyl]-ethyl ester

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In tetrahydrofuran for 12h; Ambient temperature;	98%

: 18997-19-8
Chloromethyl pivalate

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

: (2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraenoic acid 2,2-dimethyl-propionyloxymethyl ester

Conditions

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 70℃; for 3h; Alkylation;	98%

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

: 7149-10-2
vanillylamine hydrochloride

: Retvanil

Conditions

Conditions	Yield
With diethyl cyanophosphonate; triethylamine In tetrahydrofuran	98%

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

: 6169-06-8
(+)-octan-2-ol

: 82838-02-6, 104013-58-3
(+)-2-octanoyl retinoate

Conditions

Conditions	Yield
With dicyclohexyl-carbodiimide In diethyl ether 1.) 0 deg C, 30 min, 2.) 25 deg C, 1 h;	96%

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

: 53839-60-4
retinoyl chloride

: 123-30-8
4-amino-phenol

: (2E,4E,6E,8E)-[3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-enyl)-nona-2,4,6,8-tetraenoylamino]-4-hydroxyphenylamide

Conditions

Conditions	Yield
With thionyl chloride; triethylamine In N,N-dimethyl-formamide	96%

...Expand

: 64-17-5
ethanol

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

: 3899-20-5
ethyl (all-E)-retinoate

Conditions

Conditions	Yield
With dicyclohexyl-carbodiimide In diethyl ether 1.) 0 deg C, 30 min, 2.) 25 deg C, 1 h;	95%
(i) N,N'-carbonyl-di-imidazole, (ii) /BRN= 1718733/, NaOEt; Multistep reaction;

: 41864-22-6
1,1'-Carbonyl-di-(1,2,4-triazole)

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

: 1-(all-trans-Retinoyl)-1,2,4-triazol

Conditions

Conditions	Yield
In acetonitrile for 1h; Heating;	95%
In N,N-dimethyl-formamide 1.) RT; 15 min, 2.) 40 deg C, 4 h;	87%

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

: 1517-69-7
(+)-α-phenethyl alcohol

: 82838-01-5, 82863-17-0
(+)-α-phenethylretinoate

Conditions

Conditions	Yield
With dicyclohexyl-carbodiimide In diethyl ether 1.) 0 deg C, 30 min, 2.) 25 deg C, 1 h;	95%

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

: 98-85-1, 1445-91-6, 1517-69-7, 13323-81-4
(-)-α-phenethyl alcohol

: 82838-01-5, 82863-17-0
(-)-α-phenethylretinoate

Conditions

Conditions	Yield
With dicyclohexyl-carbodiimide In diethyl ether 1.) 0 deg C, 30 min, 2.) 25 deg C, 1 h;	95%

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

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

: 73880-09-8
all-trans-retinoic acid-2,3,4,6-tetra-O-acetyl-β-D-glucopyranosylester

Conditions

Conditions	Yield
With pyridine; silver(l) oxide for 1.5h;	95%

: 61644-18-6
chloromethyl isobutyrate

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

: (2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraenoic acid isobutyryloxymethyl ester

Conditions

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 70℃; for 3h; Alkylation;	94%

: 5256-74-6
1,3-diethyl 2-diazopropanedioate

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

: diethyl 2-(((2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoyl)oxy)malonate

Conditions

Conditions	Yield
With bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)]} In dichloromethane at 20℃; for 0.166667h; Inert atmosphere;	93%

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

: 5-[(fluoromethyl)(4-nitrophenyl)-λ4-sulfanylidene]-2,2-dimethyl-1,3-dioxane-4,6-dione

: (2E,4E,6E,8E)-fluoromethyl 3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-enyl)nona-2,4,6,8-tetraenoate

Conditions

Conditions	Yield
With tert-butylimino-tri(pyrrolidino)phosphorane In dichloromethane at 30℃; for 0.166667h; Schlenk technique;	93%

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

: 1609100-50-6
(2-bromoethyl)(hexyl)(2-hydroxyethyl)phosphate

: 1609100-56-2
2-((2-bromoethoxy)(hexyloxy)phosphoryl)ethoxyretinoate

Conditions

Conditions	Yield
With dmap; N-ethyl-N,N-diisopropylamine; chlorotri(pyrrolidin-1-yl)phosphonium hexafluorophosphate In dichloromethane for 24h; Inert atmosphere; Reflux;	92%
With dmap; N-ethyl-N,N-diisopropylamine; chlorotri(pyrrolidin-1-yl)phosphonium hexafluorophosphate In dichloromethane for 24h; Reflux; Inert atmosphere;	92%

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

: 106-96-7
propargyl bromide

: 58508-30-8
(2E,4E,6E,8E)-prop-2-yn-1-yl 3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoate

Conditions

Conditions	Yield
With caesium carbonate In tetrahydrofuran at 20℃; for 1h;	92%
With caesium carbonate In tetrahydrofuran at 20℃;	89%

: 1273-86-5
1-ferrocenylmethanol

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

: ferrocenylmethylretinoate

Conditions

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 2h; Inert atmosphere;	92%
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 2h; Inert atmosphere;

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

: 123-08-0
4-hydroxy-benzaldehyde

: 80850-73-3
4-formylphenyl(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-enyl)nona-2,4,6,8-tetraenoate

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 20℃; for 24h;	91%
With dmap; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 20℃; for 24h;	91%

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

: 107-15-3
ethylenediamine

: 1333107-97-3
C22H34N2O

Conditions

Conditions	Yield
Stage #1: all-trans-retinoic-acid With 1-hydroxy-pyrrolidine-2,5-dione; dicyclohexyl-carbodiimide In dimethyl sulfoxide at 20℃; for 20h; Stage #2: ethylenediamine In dimethyl sulfoxide at 20℃; for 24h;	91%
Stage #1: all-trans-retinoic-acid With 1-hydroxy-pyrrolidine-2,5-dione; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane Cooling with ice; Stage #2: ethylenediamine In dichloromethane at 20℃;	63%

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

: 83802-77-1
retinoyl fluoride

Conditions

Conditions	Yield
With (2-chloro-1,2,2-trifluoro-ethyl)-diethyl-amine In tetrahydrofuran for 0.25h; Heating;	90%
With perfluoropropylene; diethylamine
With diethylamino-sulfur trifluoride In diethyl ether 1.) -70 deg C, 60 min, 2.) r.t., 2 h;	9.1 g

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

: 2577-90-4
methyl (2S)-2-amino-3-phenylpropanoate

: 110683-03-9
N-(all-trans-retinoyl)-L-phenylalanine methyl ester

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane for 0.5h; Ambient temperature;	90%

: 6066-82-6
1-hydroxy-pyrrolidine-2,5-dione

EDAC [ethyl-3-(3-dimethylamino)propyl carbodiimide]: EDAC [ethyl-3-(3-dimethylamino)propyl carbodiimide]

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

: Retinoic Acid N-Hydroxysuccinimide Ester

Conditions

Conditions	Yield
With sodium chloride; argon In ethyl acetate; N,N-dimethyl-formamide	90%
With sodium chloride In ethyl acetate; N,N-dimethyl-formamide	90%

...Expand

: 6066-82-6
1-hydroxy-pyrrolidine-2,5-dione

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

: 65646-64-2
N-(all-trans-Retinoyloxy)-succinimide

Conditions

Conditions	Yield
With dicyclohexyl-carbodiimide In tetrahydrofuran at 0 - 20℃; Inert atmosphere; Darkness;	90%
With dicyclohexyl-carbodiimide In tetrahydrofuran at 0 - 25℃; for 0.208333h;	73%
With dicyclohexyl-carbodiimide In dimethyl sulfoxide at 20℃; for 72h;
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap In dichloromethane at 20℃; for 3h;
With dicyclohexyl-carbodiimide In tetrahydrofuran at 0 - 20℃;

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

: 109-78-4
3-Hydroxypropionitrile

: 1225383-34-5
(2E,4E,6E,8E)-2-cyanoethyl 3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-enyl)nona-2,4,6,8-tetraenoate

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 18h;	90%

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

: 2450-71-7
Propargylamine

: (2E,4E,6E,8E)-N-(propargyl)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenamide

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 20℃; Inert atmosphere;	90%

Tretinoin Consensus Reports

Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.

Tretinoin Specification

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.

Product Name

Tretinoin

Synthetic route

Tretinoin Consensus Reports

Tretinoin Specification

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