Retinal

Base Information

• Chemical Name: Retinal
• CAS No.: 116-31-4
• Deprecated CAS: 7058-59-5
• Molecular Formula: C20H28O
• Molecular Weight: 284.442
• Hs Code.: 29122990
• European Community (EC) Number: 204-135-8
• NSC Number: 626581,122757,122756,20811
• UNII: RR725D715M
• DSSTox Substance ID: DTXSID5025998
• Nikkaji Number: J1.003.612G,J1.321.772F,J1.826.581H,J121.827A,J196.192F,J439.005I,J464.833A,J464.834J,J464.835H,J490.501F,J5.279E,J861.440G
• Wikipedia: Retinal
• Wikidata: Q28529715
• NCI Thesaurus Code: C68300
• RXCUI: 2268087
• Pharos Ligand ID: LKWHWBPX78HY
• Metabolomics Workbench ID: 29026
• ChEMBL ID: CHEMBL81379
• Mol file: 116-31-4.mol

Synonyms:11 cis Retinal;11 trans Retinal;11-cis-Retinal;11-trans-Retinal;3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-Nonatetraenal;Aldehydde, Retinyl;Aldehyde, Vitamin A;all trans Retinal;all-trans-Retinal;Axerophthal;Retinal;Retinaldehyde;Retinene;Retinyl Aldehydde;Vitamin A Aldehyde

Chemical Property of Retinal

Chemical Property:

• Appearance/Colour: Yellow powder
• Vapor Pressure: 2.61E-07mmHg at 25°C
• Melting Point: 61-63 °C
• Refractive Index: 1.54
• Boiling Point: 421.4°C at 760 mmHg
• Flash Point: 205.4°C
• PSA: 17.07000
• Density: 0.948g/cm³
• LogP: 5.71690
• Storage Temp.: −20°C
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• Water Solubility.: <70mg/L(25 oC)
• XLogP3: 6.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 5
• Exact Mass: 284.214015512
• Heavy Atom Count: 21
• Complexity: 522

Purity/Quality:

99.3% ^*data from raw suppliers

all trans-Retinal ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-38
• Safety Statements: 22-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C(CCC1)(C)C)C=CC(=CC=CC(=CC=O)C)C
• Isomeric SMILES: CC1=C(C(CCC1)(C)C)/C=C/C(=C/C=C/C(=C/C=O)/C)/C
• Uses: Corotenoid component of the visual pigments. All-trans retinal is converted to retinoic acid in vivo by the action of retinal dehydrogenase. All trans-Retinal has been used:in optogenetic experiments in electrophysiological experimentto study the effect of AKR1B10 (aldo-keto reductase (AKR) superfamily member) on the conversion of retinal to retinol in the airway epitheliumin decidual transformation of human endometrial stromal cells retinaldehyde is a mild retinoid credited with increasing epidermal thickness without producing erythema.

Technology Process of Retinal

There total 193 articles about Retinal which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 10.0%

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)

Guidance literature:

With iodine; dimethyl sulfoxide; dicyclohexyl-carbodiimide;

Reference yield:

beta-carotene (7235-40-7) → 12'-apo-β-caroten-12'-al (1638-05-7) + all-trans-Retinal (116-31-4) + 4,9,13-trimethyl-15-(2,6,6-trimethylcyclohex-1-enyl)pentadeca-2,4,6,8,10,12,14-heptaenal (640-49-3)

Guidance literature:

With tert.-butylhydroperoxide; Ru[5,15-bis(tolyl)-10,20-bis(6-O-β-cyclodextryl)porphyrin]; In hexane; chloroform; water; for 24h;

DOI:10.1002/(SICI)1521-3773(20000403)39:7<1267::AID-ANIE1267>3.0.CO;2-7

Reference yield:

(S)-2-[(2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraen-(E)-ylideneamino]-4-methylsulfanyl-butyric acid → L-methionine (63-68-3,26062-47-5,58576-49-1) + all-trans-Retinal (116-31-4)

Guidance literature:

With phosphate buffer; Rate constant; also hydrolysis in physiological solution and aq. EtOH;

upstream raw materials:

3,3-dimethyl acrylaldehyde

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

beta-carotene

RETINOL

Downstream raw materials:

beta-carotene

benzoic acid-(all-trans-retinylidenehydrazide)

3.7-dimethyl-1t-(2.2.6-trimethyl-cyclohexen-(6)-yl)-dodecapentaen-(1.3t.5t.7t.9ξ)-one-(11)

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

Refernces

• 1、 Yuzawa, Tetsuro,Hamaguchi, Hiro-o. "Triplet quantum chain process in the photoisomerization of 9-cis retinal as revealed by nanosecond time-resolved infrared spectroscopy". . p. 414 - 418. Retrieved 2010.
• 2、 Oroshnik et al.. "". . p. 578. Retrieved 1956.
• 3、 Hruszkewycz, Damian P.,Cavanaugh, Kathryn R.,Takamura, Kathryn T.,Wayman, Lora M.,Curley Jr., Robert W.. "Efficient, low-cost synthesis of retinal (Vitamin A aldehyde)". . p. 2205 - 2207. Retrieved 2011.
• 4、 Becker, Ralph S.,Freedman, Kenn,Lenoble, Christian. "Photophysical and Photochemical Behavior of 11-cis-Retinal and Its Schiff Base in a Micelle". . p. 4334 - 4336. Retrieved 1986.
• 5、 Ganapathy,Liu. "Photoisomerization of polyenes. 30. Quantum chain processes in photoisomerization of the all-trans, 7-cis, and 11-cis isomers of retinal". . p. 3459 - 3464. Retrieved 1992.
• 6、 Acton, Nancy,Brossi, Arnold. "146. Retro-Aldol Reaction of Retinylidene-1,3-Diketones; Correlation with Biological Activity". . p. 1396 - 1399. Retrieved 1980.
• 7、 Duhamel, Lucette,Guillemont, Jerome,Gallic, Yann Le,Ple, Gerard,Poirier, Jean-Marie,et al.. "Polyunsaturated aldehydes by direct polyvinylogation of carbonyl compounds using functionalized phosphonates.". . p. 3129 - 3132. Retrieved 1990.
• 8、 Finkelshtein,Krasnokutskaya. "Reactivity of retinoids and carotenoids in autoxidation". . p. 411 - 418. Retrieved 1996.
• 9、 Sui, Xuewu,Farquhar, Erik R.,Hill, Hannah E.,von Lintig, Johannes,Shi, Wuxian,Kiser, Philip D.. "Preparation and characterization of metal-substituted carotenoid cleavage oxygenases". . p. 887 - 901. Retrieved 2018.
• 10、 DeGrip, Willem J.,Bovee-Geurts, Petra H. M.,Wang, Yajie,Verhoeven, Michiel A.,Lugtenburg, Johan. "Cyclopropyl and isopropyl derivatives of 11- cis and 9- cis retinals at C-9 and C-13: Subtle steric differences with major effects on ligand efficacy in rhodopsin". . p. 383 - 390. Retrieved 2011.