116-31-4

Basic information

• Product Name: ALL-TRANS-RETINAL
• Synonyms: (2E,4E,6E,8E)-3,7-diMethyl-9-(2,6,6-triMethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenal;Retinylaldehyde;2,4,6,8-Nonatetraenal, 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-;2,4,6,8-Nonatetraenal, 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-, (all-E)-;all-E-Retinal;all-trans-retina;All-trans-Retinaldehyde;alpha-Retinene
• CAS NO: 116-31-4
• Molecular Formula: C₂₀H₂₈O
• Molecular Weight: 284.44
• EINECS: 204-135-8
• Product Categories: Vitamins;Intermediates & Fine Chemicals;Pharmaceuticals;Retinoids;Aldehydes;Antitumor Agents;Building Blocks;C13-C60;Cancer Research;Carbonyl Compounds;Chemical Synthesis;Cofactor;Gene Regulation;Isoprenoid;Metabolic Pathways;Metabolites and Cofactors on the Metabolic Pathways Chart;Metabolomics;Nutrition Research;Organic Building Blocks;Vitamin A
• Mol File: 116-31-4.mol
• Article Data: 92

Chemical Properties

• Melting Point: 61-63°C
• Boiling Point: 366.92°C (rough estimate)
• Flash Point: 205.4°C
• Appearance: yellow/powder
• Density: 1.0083 (rough estimate)
• Vapor Pressure: 2.61E-07mmHg at 25°C
• Refractive Index: 1.4500 (estimate)
• Storage Temp.: −20°C
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• Water Solubility: <70mg/L(25 oC)
• Stability: Hygroscopic, Light Sensitive, Temperature Sensitive
• CAS DataBase Reference: ALL-TRANS-RETINAL(CAS DataBase Reference)
• NIST Chemistry Reference: ALL-TRANS-RETINAL(116-31-4)
• EPA Substance Registry System: ALL-TRANS-RETINAL(116-31-4)

Safety Data

• Hazard Codes: Xn
• Statements: 22-38
• Safety Statements: 22-36/37
• WGK Germany: 3
• RTECS: VH6407000
• Hazardous Substances Data: 116-31-4(Hazardous Substances Data)

Usage

Uses

Used in Vision:
ALL-TRANS-RETINAL is used as a component of the visual pigments, contributing to the proper functioning of the visual system. It is converted to retinoic acid in vivo by the action of retinal dehydrogenase.
Used in Optogenetics and Electrophysiology:
ALL-TRANS-RETINAL is used as an experimental compound in optogenetic experiments and electrophysiological studies, aiding in understanding the effects of various factors on retinal conversion and related processes.
Used in Airway Epithelium Research:
ALL-TRANS-RETINAL is used as a research compound to study the effect of AKR1B10 (aldo-keto reductase superfamily member) on the conversion of retinal to retinol in the airway epithelium, providing insights into the role of retinaldehyde in respiratory health.
Used in Decidual Transformation of Human Endometrial Stromal Cells:
ALL-TRANS-RETINAL is used as a research tool to investigate decidual transformation in human endometrial stromal cells, which is essential for understanding the role of retinaldehyde in reproductive health.
Used in Skin Care:
ALL-TRANS-RETINAL is used as an ingredient in the skincare industry for its mild retinoid properties. It is credited with increasing epidermal thickness without producing erythema, making it a valuable component in anti-aging and skin rejuvenation products.

Synthesis Reference(s)

Tetrahedron Letters, 29, p. 419, 1988 DOI: 10.1016/S0040-4039(00)80111-2

Biological Activity

all-trans retinal, also known as vitamin a aldehyde or retinaldehyde, is one of the many forms of vitamin a and also the oxidation product of all-trans retinol [1]. all-trans retinal are associated with one of the two isoforms of cellular retinol-binding proteins (crbp-i and crbp-ii) with kd values of 50 and 90 nm, respectively [1].crbp-i and crbp-ii were the first intracellular retinoid-binding proteins. both proteins display a similar binding affinity towards retinal. they play important roles in retinoid biology and regulation of the metabolism of retinol and retinal. crbp-i is used to regulate vitamin a storage and synthesis of retinoic acid. and crbp-ii has a role in the initial processing of retinol from food [1].all-trans retinal is one form of vitamin a. all-trans retinal, the initial substrate of retinoid cycle, is a chemically reactive aldehyde that can form toxic conjugates with proteins and lipids, leading to degeneration of the retina [2].

Biochem/physiol Actions

All-trans retinal is converted to retinoic acid in vivo by the action of retinal dehydrogenase. Retinoic acid is a ligand for both the retinoic acid receptor (RAR) and the retinoid X receptor (RXR) that act as transcription factors to regulate the growth and differentiation of normal and malignant cells. Retinal isomers are also chromophores that bind to opsins, a family of G-protein-linked transmembrane proteins, to form photosensitive receptors in visual and nonvisual systems. All-trans retinal is a potent photosensitizer.

Purification Methods

The aldehyde is separated from retinol by column chromatography on water-deactivated alumina. Elute with 1-2% acetone in hexane, or on TLC plates of silica gel G and using the same eluting solvent. It crystallises from pet ether or n-hexane as yellow-orange crystals, and the UV in hexane has max at 373nm (A1cm 1% 1,548) and 368nm ( 48,000). It is an irritant and is light sensitive. Store it in sealed ampoules under N2. The semicarbazone forms yellow crystals from CHCl3/Et2O or EtOH, m 199-201o(dec). The 9-cis-isomer [514-85-2] and the 13-cis-isomer [472-86-6] [max at 375nm ( 1,250) in EtOH] are also available commercially. [Beilstein 7 III 1742.]

references

[1]. noy n. retinoid-binding proteins: mediators of retinoid action. biochem j. 2000 jun 15;348 pt 3:481-95.[2]. kiser pd, golczak m, maeda a, et al. key enzymes of the retinoid (visual) cycle in vertebrate retina. biochim biophys acta. 2012 jan;1821(1):137-51.

InChI:InChI=1/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+

Synthetic route

9-trans-13-trans-dimethyl-7-(1,1,5-trimethyl-5-cyclohexen-6-yl)-7,9,11,13-nonatetraene-15-nitrile (20638-88-4) → all-trans-Retinal (116-31-4)

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 → all-trans-Retinal (116-31-4)

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

retinylidene-acetylacetone → all-trans-Retinal (116-31-4)

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

13-cis-vitamin A aldehyde (472-86-6) → all-trans-Retinal (116-31-4)

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;

all-trans-retinylidene dimedone (70424-15-6) → all-trans-Retinal (116-31-4) + dimedone (126-81-8)

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%

RETINOL (68-26-8) → all-trans-Retinal (116-31-4)

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%

3,7-dimethyl-9-phenylsulfonyl-9-<2,6,6-trimethylcyclohex-1-enyl>nona-2,4,6-trienal (150542-38-4) → all-trans-Retinal (116-31-4)

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

RETINOL (68-26-8) → 13-cis-vitamin A aldehyde (472-86-6) + all-trans-Retinal (116-31-4)

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

beta-carotene (7235-40-7) → all-trans-Retinal (116-31-4)

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

RETINOL (68-26-8) + pivalaldehyde (630-19-3) → 2,2-dimethyl-propanol-1 (75-84-3) + all-trans-Retinal (116-31-4)

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

2,2-dimethyl-4-pentenal (5497-67-6) + RETINOL (68-26-8) → 2,2-dimethylpent-4-en-1-ol (3420-42-6) + all-trans-Retinal (116-31-4)

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

(2E,6E,8E)-4-Chloro-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,6,8-trienal → all-trans-Retinal (116-31-4)

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

all-trans-retinal propylene dithioacetal (142893-61-6) → 13-cis-vitamin A aldehyde (472-86-6) + all-trans-Retinal (116-31-4)

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 → all-trans-Retinal (116-31-4)

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

retinylidene-1,3-cycloheptanedione → all-trans-Retinal (116-31-4)

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

(trimethyl-2,6,6 cyclohexene-1 yl)-9 dimethoxy-1,1 dimethyl-3,7 hydroxy-7 nonatriene-3,5,8 (111728-21-3) → all-trans-Retinal (116-31-4)

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

(trimethyl-2,6,6 cyclohexene-1 yl)-9 diethoxy-1,1 dimethyl-3,7 hydroxy-7 nonatriene-3,5,8 (74399-43-2) → all-trans-Retinal (116-31-4)

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

vitamin A aldehyde (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) → 13-cis-vitamin A aldehyde (472-86-6) + all-trans-Retinal (116-31-4)

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%

9-cis-retro-γ-retinal (66901-09-5) → all-trans-Retinal (116-31-4)

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

11,12-tetrahydroretinal (41889-27-4) → all-trans-Retinal (116-31-4)

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

(3E,5E,7E)-6-methyl-8-(2,6,6-trimethyl-1-cyclohexenyl)-3,5,7-octatriene-2-one (17974-57-1) + α-(Trimethylsilyl)-tert-butylacetaldimine (73198-78-4) → 13-cis-vitamin A aldehyde (472-86-6) + all-trans-Retinal (116-31-4)

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

(2E,4E,6E)-3,7-dimethyl-9-(2',6',6'-trimethylcyclohex-1'-en-1'-yl)nona-2,4,6-trienal (75917-44-1) → all-trans-Retinal (116-31-4)

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 → all-trans-Retinal (116-31-4)

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

12,14-retro-retinol (74916-02-2) → 9-cis vitamin A aldehyde (514-85-2) + 13-cis-vitamin A aldehyde (472-86-6) + all-trans-Retinal (116-31-4) + 9-cis,13-cis-retinal (23790-80-9)

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%

Retinol acetate (127-47-9) → 13-cis-vitamin A aldehyde (472-86-6) + all-trans-Retinal (116-31-4)

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

RETINOL (68-26-8) → C19H27O2N + C19H27O2N + all-trans-Retinal (116-31-4) + (3E,5E,7E)-6-methyl-8-(2,6,6-trimethyl-1-cyclohexenyl)-3,5,7-octatriene-2-one (17974-57-1)

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

3,3-dimethyl acrylaldehyde (107-86-8) + (2E,4E)-3-methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadienal (3917-41-7) → all-trans-Retinal (116-31-4)

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) → all-trans-Retinal (116-31-4)

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

(E)-β-ionone (79-77-6) + ((2E,4E)-5-[1,3]Dioxolan-2-yl-4-methyl-penta-2,4-dienyl)-phosphonic acid diethyl ester (129975-66-2) → all-trans-Retinal (116-31-4)

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;

methanol (67-56-1) + all-trans-Retinal (116-31-4) → all-trans-methyl retinoate (339-16-2)

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

all-trans-Retinal (116-31-4) + 6(I)-amino-6(I)-deoxycyclomaltoheptaose (29390-67-8) → C62H97NO34

Conditions	Yield
With acetic acid In dimethyl sulfoxide	98%

all-trans-Retinal (116-31-4) + N-butylamine (109-73-9) → trans-N-retinylidene-n-butylimine (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)

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;

diethoxyphosphoryl-acetic acid ethyl ester (867-13-0) + all-trans-Retinal (116-31-4) → ethyl (2E,4E,6E,8E,10E)-5,9-dimethyl-11-(2,6,6-trimethylcyclohexen-1-yl)-2,4,6,8,10-undecapentaenoate (13979-19-6)

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%

Tetraethyl methylenediphosphonate (1660-94-2) + all-trans-Retinal (116-31-4) → 4,8-dimethyl-10-(2,6,6-trimethyl-1-cyclohex-1-enyl)-deca-1,3,5,7,9-pentaenyl-diethyl phosphonate

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%

BARBITURIC ACID (67-52-7) + all-trans-Retinal (116-31-4) → (2E,4E,6E,8E)-5-[3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-enyl)-nona-2,4,6,8-tetraenylidene]barbituric acid

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

all-trans-Retinal (116-31-4) + 3A-amino-3A-deoxy-β-cyclodextrin (125827-01-2) → C62H97NO34

Conditions	Yield
With acetic acid In dimethyl sulfoxide	93%

4,6-dihydroxy-2-mercaptopyrimidine (504-17-6) + all-trans-Retinal (116-31-4) → 5-[3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-enyl)-nona-2E,4E,6E,8E-tetraenylidene]-2-thiobarbituric acid

Conditions	Yield
In ethanol at 45℃;	93%

1,3-dimethylbarbituric acid (769-42-6) + all-trans-Retinal (116-31-4) → 5-[3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-enyl)-nona-2E,4E,6E,8E-tetraenylidene]-1,3-dimethylbarbituric acid

Conditions	Yield
In ethanol at 45℃;	93%

N,N'-diethyl-2-thiobarbituric acid (5217-47-0) + all-trans-Retinal (116-31-4) → 5-[3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-enyl)-nona-2E,4E,6E,8E-tetraenylidene]-1,3-diethyl-2-thiobarbituric acid

Conditions	Yield
In ethanol at 45℃;	93%

7-isopropyl-1,4-dimethyl-azulene (489-84-9) + all-trans-Retinal (116-31-4) → (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	Yield
With hexafluorophosphoric acid In methanol at -10℃; for 1h;	91%

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 (70893-06-0) + all-trans-Retinal (116-31-4) → C32H47NO6

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

all-trans-Retinal (116-31-4) + tert-butyldimethylsilyl cyanide (56522-24-8) → retinal tert-butyl-dimethylsilylcyanohydrin (886226-24-0)

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%

all-trans-Retinal (116-31-4) + 1,3-cylohexanedione (504-02-9) → retinylidene-1,3-cyclohexanedione

Conditions	Yield
With piperidine In benzene Ambient temperature;	89%

all-trans-Retinal (116-31-4) + 4-Nitroanthranilic acid (619-17-0) → 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 (144459-79-0)

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

all-trans-Retinal (116-31-4) + 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	Yield
With 3 A molecular sieve In ethanol for 24h; Ambient temperature;	88%

all-trans-Retinal (116-31-4) + 1,2-diamino-benzene (95-54-5) → C26H34N2

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

all-trans-Retinal (116-31-4) + dimedone (126-81-8) → all-trans-retinylidene dimedone (70424-15-6)

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

Upstream product

• 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 
• 7235-40-7 beta-carotene 
• 564-88-5 11-cis,13-cis-retinal 
• 114968-77-3 lithio-1 methyl-2 trimethylsiloxy-4 butadiene 
• 58274-64-9 (E)-trimethyl((3-methylbuta-1,3-dien-1-yl)oxy)silane 
• 1222538-51-3 (1E,3E)-3-methyl-7-methylene-1-(2,6,6-trimethyl-cyclohex-1-enyl)-9,9-diethoxynona-1,3-dien-5-ol 
• 67711-05-1 9-cis,11-cis-retinal 
• 119718-30-8 7-cis,9-cis,11-cis-retinonitrile 
• 79-77-6 (E)-β-ionone 
• 114968-70-6 lithio-6 methyl-3 methoxy-1 hexatriene-1,3,5 
• 146918-87-8 ((E)-3-[1,3]Dioxolan-2-yl-but-2-enyl)-phosphonic acid diethyl ester 
• 54340-95-3 1,1-diethoxy-3-methyl-3-butene 
• 54717-57-6 1-methoxy-3-methyl-1, 3-butadiene 

Downstream Products

• 7235-40-7 beta-carotene 
• 6980-50-3 3.7-dimethyl-1t-(2.2.6-trimethyl-cyclohexen-(6)-yl)-dodecapentaen-(1.3t.5t.7t.9ξ)-one-(11) 
• 6980-71-8 Retinyliden-cyclopentadien 
• 121662-98-4 3-[(2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraen-(Z)-ylidene]-1,2-dimethyl-3H-indolium 
• 144459-75-6 8-[(2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraen-(Z)-ylideneamino]-octanoic acid 
• 73685-26-4 retinylidene-1,3-cyclooctanedione 

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Neuroprotective effect of tetramethylpyrazine against ALL-TRANS-RETINAL (cas 116-31-4) toxicity in the differentiated Y-79 cells via upregulation of IRBP expression08/26/2019

It is estimated that abnormal accumulation of all-trans-retinal (atRAL) is a leading cause of photoreceptor degeneration in retinal degenerative diseases. Deficiency of interphotoreceptor retinoid-binding protein (IRBP), a retinoid transporter in the visual cycle, is responsible for the impaired...detailed

Isolation of the retinal isomers from the isomerization of ALL-TRANS-RETINAL (cas 116-31-4) by flash countercurrent chromatography☆08/24/2019

The isolation of the retinal isomers from all-trans-retinal was performed by flash countercurrent chromatography. In each separation, isomerization reaction solution of 200 mg all-trans-retinal could be loaded on a 1200 mL of high-speed countercurrent chromatographic column with 5 mm bore, elute...detailed

ALL-TRANS-RETINAL (cas 116-31-4) dimer formation alleviates the cytotoxicity of ALL-TRANS-RETINAL (cas 116-31-4) in human retinal pigment epithelial cells08/22/2019

Effective clearance of all-trans-retinal (atRAL) from retinal pigment epithelial (RPE) cells is important for avoiding its cytotoxicity. However, the metabolism of atRAL in RPE cells is poorly clarified. The present study was designed to analyze metabolic products of atRAL and to compare the cyt...detailed

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The OSM (Oxidation State Modification) Concept: Application to a New and Rapid Synthesis of Retinoids

The OSM (oxidation state modification) concept for the elaboration of new synthetic pathways is demonstrated for the synthesis of β-ionylidene acetaldehyde 11 and retinal 13.According to this new scheme, electrophilic addition to ω-heterosubstituted enol ethers 5 of the cationic species 9, generated from β-ionol led to aldehydic intermediates 10 which undergo easy elimination to β-ionylidene acetaldehyde 11.Similarly, retinal 13 was obtained from vinyl-β-ionol 14 and dienol ethers 12, via aldehydes 16.

Triplet quantum chain process in the photoisomerization of 9-cis retinal as revealed by nanosecond time-resolved infrared spectroscopy

The mechanism of the photoisomerization of 9-cis retinal has been studied by nanosecond time-resolved infrared spectroscopy. A cyclohexane solution of 9-cis retinal was photoexcited at 349 nm and the subsequent photodynamics were traced. A singular value decomposition (SVD) analysis of the time-resolved infrared data shows that there are two distinct isomerization pathways. One is the triplet pathway that takes place in the picosecond time regime from 9-cis to all-trans. The other involves the energy transfer between the all-trans triplet state and the 9-cis ground state with the resultant 9-cis triplet state subsequently reproducing the all-trans by fast isomerization on the triplet potential surface. This quantum chain process occurs in the microsecond time regime.

Mechanism for the Two-bond Isomerization in the Photoirradiation of 7,9-Di-cis-retinal

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The isomeric composition of retinal was measured in a number of bacteriorhodopsin (bR) mutants (D85N), D212N, R82A, Y185F, and D115N) under various conditions, using a rapid retinal extraction technique followed by HPLC analysis. Besides the 13-cis and the all-trans retinal isomers observed in wild type (wt) bR under physiological conditions, the 11-cis and 9-cis retinal isomers were observed in variable but minor amounts in the bR mutants. In addition, the values of the equilibrium constant at two temperatures and the enthalpy change for the all-trans to 13-cis isomerization process in the dark-adapted state of D212N, D85N, deionized blue bR, and wt bR were determined. We find that perturbation of the retinal cavity (pocket) by residue replacement changes the relative thermal stability of the different retinal isomers, allowing for thermal-and/or photoisomerization of the retinal chromophore along C9-C10 and C11-C12 bonds to moderately compete with the isomerization around the C13-C14 bond. The bR mutants expressed in Halobacterium salinarium studied in the present work showed normal 13-cis to all-trans light adaptation, in contrast with abnormal all-trans to 13-cis light adaptation observed for D212E, D212A, and D212N expressed in Escherichia coli, suggesting an influence of the purple membrane lattice and/or the lipids on the stability of the different retinal isomers within the protein.

Photophysical and Photochemical Behavior of 11-cis-Retinal and Its Schiff Base in a Micelle

The photophysical and photochemical behaviors of 11-cis-retinal and its Schiff base have been studied in a micelle made from Triton X-100.Both microsecond laser flash and steady-state techniques were employed.The photoisomerization yield (ca. 0.19) and the triplet quantum yield (ca. 0.13) were determined in the case of 11-cis-retinal.In the case of the 11-cis Schiff base, a long-lived (240 s) non-excited-state transient was seen and very little isomerization appears to have occured.The relative location of the 11-cis-retinal and its Schiff base in the micelle could be determined.The retinal was found to be in a polar region, Stern layer, of the micelle while the 11-cis Schiff base was found to be located in a dry, hydrocarbon-core region of the micelle.The nonionic micellar environment did not favor in any manner the photoisomerization of the 11-cis-retinal or the 11-cis Schiff base compared to any other solvents (polar or nonpolar).

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