trans-Retinal supplier | CasNO.116-31-4

Name
ALL-TRANS-RETINAL
EINECS 204-135-8
CAS No. 116-31-4
Article Data125
CAS DataBase
Density 0.948g/cm³
Solubility <70mg/L(25 oC)
Melting Point 61-63 °C
Formula C₂₀H₂₈O
Boiling Point 421.4°C at 760 mmHg
Molecular Weight 284.442
Flash Point 205.4°C
Transport Information
Appearance Yellow powder
Safety 22-36/37
Risk Codes 22-38
Molecular Structure
Hazard Symbols Xn
Synonyms Retinal,all-trans- (8CI);Retinene 1 (6CI);(all-E)-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenal;2,4,6,8-Nonatetraenal, 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-,(all-E)-;Axerophthal;E-Retinal;Retinaldehyde;Retinene;Vitamin A aldehyde;Vitamin A1 aldehyde;all-E-Retinal;all-trans-Retinal;all-trans-Retinaldehyde;all-trans-Vitamin A aldehyde;trans-Retinal;trans-Vitamin A aldehyde;
PSA 17.07000
LogP 5.71690

Synthetic route

: 20638-88-4
9-trans-13-trans-dimethyl-7-(1,1,5-trimethyl-5-cyclohexen-6-yl)-7,9,11,13-nonatetraene-15-nitrile

: 116-31-4
all-trans-Retinal

Conditions

Conditions	Yield
With diisobutylaluminium hydride In hexane; Petroleum ether at -60 - -20℃; for 1h;	95%
With diisobutylaluminium hydride In toluene at -5 - 0℃; for 1h; Inert atmosphere;	26.2%

: retinylidene-1,3-cyclooctanedione

: 116-31-4
all-trans-Retinal

Conditions

Conditions	Yield
With methylamine In water; benzene for 0.333333h; Product distribution; Ambient temperature; retro-Knoevenagel fragmentation;	93%

: retinylidene-acetylacetone

: 116-31-4
all-trans-Retinal

Conditions

Conditions	Yield
With methylamine In water; benzene for 0.5h; Product distribution; Ambient temperature; retro-Knoevenagel fragmentation;	92%

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

: 116-31-4
all-trans-Retinal

Conditions

Conditions	Yield
With iodine In diethyl ether; benzene for 48h; Ambient temperature;	91%
In benzene-d6 at 80℃;	10%
With silica gel In cyclohexane Quantum yield; Irradiation; excitation wavelength;
With iodine In n-heptane at 40℃; Rate constant;

: 70424-15-6
all-trans-retinylidene dimedone

A: 116-31-4
all-trans-Retinal

B: 126-81-8
dimedone

Conditions

Conditions	Yield
With methylamine In water; benzene for 0.25h; Product distribution; Mechanism; Ambient temperature; retro-Knoevenagel fragmentation; variation of reaction conditions;	A 91% B 75%

: 68-26-8
RETINOL

: 116-31-4
all-trans-Retinal

Conditions

Conditions	Yield
With manganese(IV) oxide In dichloromethane Ambient temperature;	90%
With manganese(IV) oxide; sodium carbonate In dichloromethane for 4h; Inert atmosphere;	90%
With manganese(IV) oxide	90%

: 150542-38-4
3,7-dimethyl-9-phenylsulfonyl-9-<2,6,6-trimethylcyclohex-1-enyl>nona-2,4,6-trienal

: 116-31-4
all-trans-Retinal

Conditions

Conditions	Yield
With sodium methylate In tetrahydrofuran; methanol for 240h; Ambient temperature;	90%

: 68-26-8
RETINOL

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

B: 116-31-4
all-trans-Retinal

Conditions

Conditions	Yield
With manganese(IV) oxide In dichloromethane for 12h; Inert atmosphere; Fluorescence light;	A 8% B 90%

: 7235-40-7
beta-carotene

: 116-31-4
all-trans-Retinal

Conditions

Conditions	Yield
With oxygen In water under 760.051 Torr; for 8h; Solvent; Reagent/catalyst;	89%
With osmium(VIII) oxide; diethyl ether; sodium sulfate Reagens 4: wss. H2O2;
With chloroform; dihydrogen peroxide; acetic acid
With manganese(IV) oxide

: 68-26-8
RETINOL

: 630-19-3
pivalaldehyde

A: 75-84-3
2,2-dimethyl-propanol-1

B: 116-31-4
all-trans-Retinal

Conditions

Conditions	Yield
With aluminum isopropoxide In water	A n/a B 87%
With aluminum isopropoxide In water

...Expand

: 5497-67-6
2,2-dimethyl-4-pentenal

: 68-26-8
RETINOL

A: 3420-42-6
2,2-dimethylpent-4-en-1-ol

B: 116-31-4
all-trans-Retinal

Conditions

Conditions	Yield
With aluminum isopropoxide In water	A n/a B 87%

...Expand

: (2E,6E,8E)-4-Chloro-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,6,8-trienal

: 116-31-4
all-trans-Retinal

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 50℃; for 2h;	86%

: 142893-61-6
all-trans-retinal propylene dithioacetal

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

B: 116-31-4
all-trans-Retinal

Conditions

Conditions	Yield
With N-hydroxy-2,4,6-trimethylbenzensulfonamide In dichloromethane at -95℃; for 0.166667h;	A 7 % Spectr. B 80%
With N-hydroxy-2,4,6-trimethylbenzensulfonamide In dichloromethane at -95℃; for 0.166667h; Title compound not separated from byproducts;	A 7 % Spectr. B 93 % Spectr.

: retinylidene-1,3-cyclohexanedione

: 116-31-4
all-trans-Retinal

Conditions

Conditions	Yield
With methylamine In water; benzene for 0.25h; Product distribution; Ambient temperature; retro-Knoevenagel fragmentation;	74%

: retinylidene-1,3-cycloheptanedione

: 116-31-4
all-trans-Retinal

Conditions

Conditions	Yield
With methylamine In water; benzene for 0.25h; Product distribution; Ambient temperature; retro-Knoevenagel fragmentation;	74%

: 111728-21-3
(trimethyl-2,6,6 cyclohexene-1 yl)-9 dimethoxy-1,1 dimethyl-3,7 hydroxy-7 nonatriene-3,5,8

: 116-31-4
all-trans-Retinal

Conditions

Conditions	Yield
With 2,6-di-tert-butyl-4-methyl-phenol; hydrogen bromide In acetone for 0.0833333h; Heating;	73%

: 74399-43-2
(trimethyl-2,6,6 cyclohexene-1 yl)-9 diethoxy-1,1 dimethyl-3,7 hydroxy-7 nonatriene-3,5,8

: 116-31-4
all-trans-Retinal

Conditions

Conditions	Yield
With 2,6-di-tert-butyl-4-methyl-phenol; hydrogen bromide In acetone for 0.0833333h; Heating;	72%

: 116-31-4, 472-86-6, 514-85-2, 564-87-4, 564-88-5, 1436-55-1, 23790-80-9, 24315-14-8, 34504-14-8, 52918-36-2, 56085-53-1, 56085-54-2, 56085-55-3, 67529-90-2, 67711-05-1, 67737-35-3, 67737-36-4, 67737-37-5, 67737-38-6, 67737-39-7
vitamin A aldehyde

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

B: 116-31-4
all-trans-Retinal

Conditions

Conditions	Yield
Stage #1: vitamin A aldehyde With hydroquinone In diethyl ether Heating; Inert atmosphere; Fluorescence light; Stage #2: With iodine In methanol for 1.25h; Irradiation;	A n/a B 55%

: 66901-09-5
9-cis-retro-γ-retinal

: 116-31-4
all-trans-Retinal

Conditions

Conditions	Yield
In acetonitrile for 5h; Irradiation;	49%

: 41889-27-4
11,12-tetrahydroretinal

: 116-31-4
all-trans-Retinal

Conditions

Conditions	Yield
With pyridine; palladium diacetate; potassium carbonate In N,N-dimethyl-formamide at 60℃; for 6h;	46%

: 17974-57-1
(3E,5E,7E)-6-methyl-8-(2,6,6-trimethyl-1-cyclohexenyl)-3,5,7-octatriene-2-one

: 73198-78-4
α-(Trimethylsilyl)-tert-butylacetaldimine

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

B: 116-31-4
all-trans-Retinal

Conditions

Conditions	Yield
With oxalic acid; lithium diisopropyl amide 1.) THF, -78 deg C;	A 17% B 37%

...Expand

: 75917-44-1
(2E,4E,6E)-3,7-dimethyl-9-(2',6',6'-trimethylcyclohex-1'-en-1'-yl)nona-2,4,6-trienal

: 116-31-4
all-trans-Retinal

Conditions

Conditions	Yield
With 2,3,5,6-tetrafluoro-1,4-benzoquinone In toluene at 60℃; for 24h;	29%

: retinylidene-4,6-di-t-butyl-1,3-cyclohexanedione

: 116-31-4
all-trans-Retinal

Conditions

Conditions	Yield
With methylamine In water; benzene for 24h; Product distribution; Ambient temperature; retro-Knoevenagel fragmentation;	27%

: 74916-02-2
12,14-retro-retinol

A: 514-85-2
9-cis vitamin A aldehyde

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

C: 116-31-4
all-trans-Retinal

D: 23790-80-9
9-cis,13-cis-retinal

Conditions

Conditions	Yield
With iodine; dimethyl sulfoxide; dicyclohexyl-carbodiimide	A 10% B n/a C n/a D 10%
With iodine; dimethyl sulfoxide; dicyclohexyl-carbodiimide Yield given. Yields of byproduct given;	A 10% B n/a C n/a D 10%

...Expand

: 127-47-9
Retinol acetate

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

B: 116-31-4
all-trans-Retinal

Conditions

Conditions	Yield
Stage #1: Retinol acetate With methanol; sodium Stage #2: With manganese(IV) oxide In ethyl acetate	A 8% B n/a

: 68-26-8
RETINOL

A: C19H27O2N

B: C19H27O2N

C: 116-31-4
all-trans-Retinal

D: 17974-57-1
(3E,5E,7E)-6-methyl-8-(2,6,6-trimethyl-1-cyclohexenyl)-3,5,7-octatriene-2-one

Conditions

Conditions	Yield
With peroxynitrite In tetrahydrofuran for 0.0333333h;	A 3.1% B 2.1% C 3.8% D 3.6%

...Expand

: 107-86-8
3,3-dimethyl acrylaldehyde

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

: 116-31-4
all-trans-Retinal

Conditions

Conditions	Yield
With piperidine; ethanol; acetic acid at 15 - 20℃;

: (+/-)-9-ethoxy-3.7-dimethyl-1t-(2.2.6-trimethyl-cyclohexen-(6)-yl)-nonatrien-(1.3t.5t)-yn-(8)-ol-(7)

: 116-31-4
all-trans-Retinal

Conditions

Conditions	Yield
With Pd-BaSO4; ethyl acetate Hydrogenation.Behandlung des in Aether geloesten Reaktionsprodukts mit wss. Oxalsaeure unter Stickstoff;

: 79-77-6
(E)-β-ionone

: 129975-66-2
((2E,4E)-5-[1,3]Dioxolan-2-yl-4-methyl-penta-2,4-dienyl)-phosphonic acid diethyl ester

: 116-31-4
all-trans-Retinal

Conditions

Conditions	Yield
With hydrogenchloride; potassium tert-butylate 1a) -70 deg C, THF, 90 min, 1b) -70 deg C to 0 deg C, THF, ca. 2 h, 2) -50 deg C; Yield given. Multistep reaction;

: 67-56-1
methanol

: 116-31-4
all-trans-Retinal

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

Conditions

Conditions	Yield
With potassium cyanide; manganese(IV) oxide; acetic acid In methanol for 12h; Ambient temperature;	98%

: 116-31-4
all-trans-Retinal

: 29390-67-8
6(I)-amino-6(I)-deoxycyclomaltoheptaose

: C62H97NO34

Conditions

Conditions	Yield
With acetic acid In dimethyl sulfoxide	98%

: 116-31-4
all-trans-Retinal

: 109-73-9
N-butylamine

: 36076-04-7, 51804-54-7, 51847-39-3, 52647-48-0, 61769-47-9, 68737-92-8, 68737-93-9, 68737-94-0, 74644-89-6, 80736-10-3, 92216-30-3, 98462-61-4, 100836-89-3, 120201-10-7, 34512-76-0
trans-N-retinylidene-n-butylimine

Conditions

Conditions	Yield
With 3 A molecular sieve In diethyl ether at -20℃; for 24h;	97%
In water at 20℃; Equilibrium constant; in various detergent micelles;
With phosphate buffer; phosphatidylcholine-cholesterol liposome In hexane; chloroform at 25℃; Rate constant; pH 7.1;

: 867-13-0
diethoxyphosphoryl-acetic acid ethyl ester

: 116-31-4
all-trans-Retinal

: 13979-19-6
ethyl (2E,4E,6E,8E,10E)-5,9-dimethyl-11-(2,6,6-trimethylcyclohexen-1-yl)-2,4,6,8,10-undecapentaenoate

Conditions

Conditions	Yield
Stage #1: diethoxyphosphoryl-acetic acid ethyl ester With sodium hexamethyldisilazane In tetrahydrofuran at 0℃; for 0.25h; Horner-Wadsworth-Emmons Olefination; Stage #2: all-trans-Retinal In tetrahydrofuran at 0 - 20℃; Horner-Wadsworth-Emmons Olefination; diastereoselective reaction;	96%

: 1660-94-2
Tetraethyl methylenediphosphonate

: 116-31-4
all-trans-Retinal

: 4,8-dimethyl-10-(2,6,6-trimethyl-1-cyclohex-1-enyl)-deca-1,3,5,7,9-pentaenyl-diethyl phosphonate

Conditions

Conditions	Yield
Stage #1: Tetraethyl methylenediphosphonate With sodium hydride In tetrahydrofuran for 0.5h; Metallation; Stage #2: all-trans-Retinal In tetrahydrofuran; benzene Condensation;	95%

: 67-52-7
BARBITURIC ACID

: 116-31-4
all-trans-Retinal

: (2E,4E,6E,8E)-5-[3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-enyl)-nona-2,4,6,8-tetraenylidene]barbituric acid

Conditions

Conditions	Yield
In ethanol at 45℃; for 1h;	94%

: 116-31-4
all-trans-Retinal

: 125827-01-2
3A-amino-3A-deoxy-β-cyclodextrin

: C62H97NO34

Conditions

Conditions	Yield
With acetic acid In dimethyl sulfoxide	93%

: 504-17-6
4,6-dihydroxy-2-mercaptopyrimidine

: 116-31-4
all-trans-Retinal

: 5-[3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-enyl)-nona-2E,4E,6E,8E-tetraenylidene]-2-thiobarbituric acid

Conditions

Conditions	Yield
In ethanol at 45℃;	93%

: 769-42-6
1,3-dimethylbarbituric acid

: 116-31-4
all-trans-Retinal

: 5-[3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-enyl)-nona-2E,4E,6E,8E-tetraenylidene]-1,3-dimethylbarbituric acid

Conditions

Conditions	Yield
In ethanol at 45℃;	93%

: 5217-47-0
N,N'-diethyl-2-thiobarbituric acid

: 116-31-4
all-trans-Retinal

: 5-[3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-enyl)-nona-2E,4E,6E,8E-tetraenylidene]-1,3-diethyl-2-thiobarbituric acid

Conditions

Conditions	Yield
In ethanol at 45℃;	93%

: 489-84-9
7-isopropyl-1,4-dimethyl-azulene

: 116-31-4
all-trans-Retinal

: (2E,4E,6E,8E)-1-(3-guaiazulenyl)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraen-1-ylium hexafluorophosphate

Conditions

Conditions	Yield
With hexafluorophosphoric acid In methanol at -10℃; for 1h;	91%

: 70893-06-0
N-[(3aR,5S,6R,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl]-hydroxylamine

: 116-31-4
all-trans-Retinal

: C32H47NO6

Conditions

Conditions	Yield
In benzene at 80℃; for 12h;	90%

: 116-31-4
all-trans-Retinal

: 56522-24-8
tert-butyldimethylsilyl cyanide

: 886226-24-0
retinal tert-butyl-dimethylsilylcyanohydrin

Conditions

Conditions	Yield
With lithium bromide In tetrahydrofuran at 20℃; for 20h; Inert atmosphere;	90%
With triethylamine In dichloromethane for 20h;	78%
With triethylamine In dichloromethane for 20h;	78%

: 116-31-4
all-trans-Retinal

: 504-02-9
1,3-cylohexanedione

: retinylidene-1,3-cyclohexanedione

Conditions

Conditions	Yield
With piperidine In benzene Ambient temperature;	89%

: 116-31-4
all-trans-Retinal

: 619-17-0
4-Nitroanthranilic acid

: 144459-79-0
2-[(2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraen-(Z)-ylideneamino]-4-nitro-benzoic acid

Conditions

Conditions	Yield
In methanol; dichloromethane for 2h; Ambient temperature;	89%

: 116-31-4
all-trans-Retinal

: pyrrolidinium hexafluorophosphate

: (all trans)-1-<3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenylidene>pyrrolidinium hexafluorophosphate

Conditions

Conditions	Yield
With 3 A molecular sieve In ethanol for 24h; Ambient temperature;	88%

: 116-31-4
all-trans-Retinal

: 95-54-5
1,2-diamino-benzene

: C26H34N2

Conditions

Conditions	Yield
In acetonitrile for 2h; Reflux;	87.5%

: 116-31-4
all-trans-Retinal

: 126-81-8
dimedone

: 70424-15-6
all-trans-retinylidene dimedone

Conditions

Conditions	Yield
With piperidine In toluene for 18h; Ambient temperature;	85%
With piperidine In toluene at 20℃; for 6h;	81%

trans-Retinal Consensus Reports

Reported in EPA TSCA Inventory.

trans-Retinal Specification

The trans-Vitamin A aldehyde is an organic compound with the formula C₂₀H₂₈O. The IUPAC name of this chemical is (2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenal. With the CAS registry number 116-31-4 and EINECS 204-135-8, it is also named as trans-trans-Retinal. The product's categories are Intermediates & Fine Chemicals; Pharmaceuticals; Retinoids. It is yellow powder which is corotenoid component of the visual pigments. When heated to decomposition it emits acrid smoke and irritating vapors.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 6.38; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 6.376; (4)ACD/LogD (pH 7.4): 6.376; (5)ACD/BCF (pH 5.5): 41285.77; (6)ACD/BCF (pH 7.4): 41285.77; (7)ACD/KOC (pH 5.5): 70076.586; (8)ACD/KOC (pH 7.4): 70076.586; (9)#H bond acceptors: 1; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 5; (12)Polar Surface Area: 17.07 Å²; (13)Index of Refraction: 1.541; (14)Molar Refractivity: 94.15 cm³; (15)Molar Volume: 299.844 cm³; (16)Polarizability: 37.324×10^-24 cm³; (17)Surface Tension: 35.126 dyne/cm; (18)Density: 0.949 g/cm³; (19)Flash Point: 205.369 °C; (20)Enthalpy of Vaporization: 67.544 kJ/mol; (21)Boiling Point: 421.428 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.

Preparation and Uses of trans-Vitamin A aldehyde: By the catalysis of alcohol dehydrogenase and coenzyme I, II, Vitamin A can form cis-and trans trans-Retinal. trans-Vitamin A aldehyde is used as β-carotene intermediate. It also can react with methanol to get [7t,9t,11t,13t]retinoic acid methyl ester. This reaction needs reagents KCN, MnO₂, AcOH and solvent methanol at ambient temperature. The reaction time is 12 hours. The yield is 98%.

trans-Vitamin A aldehyde can react with methanol to get [7t,9t,11t,13t]retinoic acid methyl ester

When you are using this chemical, please be cautious about it as the following:
It is not only harmful if swallowed, but also irritating to skin. So people should not breathe dust. If you want to contact this product, you must wear suitable protective clothing and gloves.

People can use the following data to convert to the molecule structure.
1. Canonical SMILES: CC1=C(C(CCC1)(C)C)C=CC(=CC=CC(=CC=O)C)C
2. Isomeric SMILES: CC1=C(C(CCC1)(C)C)/C=C/C(=C/C=C/C(=C/C=O)/C)/C
3. InChI: InChI=1S/C20H28O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6,8-9,11-13,15H,7,10,14H2,1-5H3/b9-6+,12-11+,16-8+,17-13+
4. InChIKey: NCYCYZXNIZJOKI-OVSJKPMPSA-N

Product Name

ALL-TRANS-RETINAL

Synthetic route

trans-Retinal Consensus Reports

trans-Retinal Specification

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