Retinal | CAS#116-31-4 | Vitamin A derivative

MedKoo Cat#: 463285 | Name: Retinal

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Retinal is one of the major derivatives of vitamin A group. A variety of food serves as a source of vitamin A. It is predominant in liver and among the brightly colored vegetables.

Chemical Structure

Retinal

CAS#116-31-4

Theoretical Analysis

MedKoo Cat#: 463285

Name: Retinal

CAS#: 116-31-4

Chemical Formula: C20H28O

Exact Mass: 284.2140

Molecular Weight: 284.44

Elemental Analysis: C, 84.45; H, 9.92; O, 5.62

Price and Availability

Size	Price	Availability
25mg	USD 350.00	2 Weeks
100mg	USD 550.00	2 Weeks
500mg	USD 1,250.00	2 Weeks

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Related CAS #

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Synonym

Retinal; Retinaldehyde; NSC 122757; NSC122757; NSC-122757; NSC 626581; NSC626581; NSC-626581; Vitamin A aldehyde; all-trans-Retinal; all trans-Retinal;

IUPAC/Chemical Name

(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenal

InChi Key

NCYCYZXNIZJOKI-OVSJKPMPSA-N

InChi Code

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+

SMILES Code

CC(/C=C/C=C(/C=C/C1=C(CCCC1(C)C)C)C)=C\C=O

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO, DMF, and ethanol

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO, DMF, and ethanol

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Retinal is the oxidation product of all-trans retinol and associates with cellular retinol-binding protein-I (CRBP-I) and CRBP-II (Kds = 50 and 90 nM, respectively), which are involved in the intracellular transport of retinol. Retinal is an intermediate of the phototransduction pathway of photoreceptors, including rhodopsin and bacterial opsins. As a chemically reactive aldehyde, all-trans retinal can form toxic conjugates with proteins and lipids, leading to degeneration of the retina.

In vitro activity:

Retinal activates NLRP3 inflammasome and autophagy in THP-1 cells. Increasing levels of autophagy leads to the inhibition of excessive NLRP3 inflammasome activation. These findings shed new light on the pathogenesis of age-related retinal degeneration. Reference: Am J Transl Res. 2023 Jun 15;15(6):4380-4389. https://pubmed.ncbi.nlm.nih.gov/37434849/

In vivo activity:

In 23 Korean volunteers, all objective parameters, including wrinkle depth, were significantly improved in both multilamellar vesicle containing retinal (MLV-RAL) and retinol treated sides. Compared with the retinol-treated side, MLV-RAL showed a significant improvement of objective assessments except for dermal density. MLV-RAL cream improved wrinkle, facial contour, and biophysical parameters associated with skin aging. Reference: J Cosmet Dermatol. 2021 Sep;20(9):2874-2879. https://pubmed.ncbi.nlm.nih.gov/33569865/

	Solvent	mg/mL	mM
Solubility
	DMF	25.0	87.89
	DMSO	16.0	56.25
	Ethanol	25.0	87.89

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 284.44 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Xia Q, Li J, Zhang L, Zhou Y, Yang Z, Xie J. Increasing autophagy ameliorates all-trans-retinal-activated NLRP3 inflammasomes in human THP-1 macrophages. Am J Transl Res. 2023 Jun 15;15(6):4380-4389. PMID: 37434849; PMCID: PMC10331683. 2. Park JW, Jung KH, Lee JH, Moon SH, Cho YS, Lee KH. Inhibition of aldehyde dehydrogenase 1 enhances the cytotoxic effect of retinaldehyde on A549 cancer cells. Oncotarget. 2017 Jul 25;8(59):99382-99393. doi: 10.18632/oncotarget.19544. PMID: 29245909; PMCID: PMC5725100. 3. Kim J, Kim J, Jongudomsombat T, Kim Bs E, Suk J, Lee D, Lee JH. The efficacy and safety of multilamellar vesicle containing retinaldehyde: A double-blinded, randomized, split-face controlled study. J Cosmet Dermatol. 2021 Sep;20(9):2874-2879. doi: 10.1111/jocd.13993. Epub 2021 Feb 18. PMID: 33569865. 4. Nallamshetty S, Le PT, Wang H, Issacsohn MJ, Reeder DJ, Rhee EJ, Kiefer FW, Brown JD, Rosen CJ, Plutzky J. Retinaldehyde dehydrogenase 1 deficiency inhibits PPARγ-mediated bone loss and marrow adiposity. Bone. 2014 Oct;67:281-91. doi: 10.1016/j.bone.2014.07.005. Epub 2014 Jul 24. PMID: 25064526; PMCID: PMC4209126.

In vitro protocol:

In vivo protocol:

1. Kim J, Kim J, Jongudomsombat T, Kim Bs E, Suk J, Lee D, Lee JH. The efficacy and safety of multilamellar vesicle containing retinaldehyde: A double-blinded, randomized, split-face controlled study. J Cosmet Dermatol. 2021 Sep;20(9):2874-2879. doi: 10.1111/jocd.13993. Epub 2021 Feb 18. PMID: 33569865. 2. Nallamshetty S, Le PT, Wang H, Issacsohn MJ, Reeder DJ, Rhee EJ, Kiefer FW, Brown JD, Rosen CJ, Plutzky J. Retinaldehyde dehydrogenase 1 deficiency inhibits PPARγ-mediated bone loss and marrow adiposity. Bone. 2014 Oct;67:281-91. doi: 10.1016/j.bone.2014.07.005. Epub 2014 Jul 24. PMID: 25064526; PMCID: PMC4209126.

1: Reboussin É, Bastelica P, Benmessabih I, Cordovilla A, Delarasse C, Réaux-Le Goazigo A, Brignole-Baudouin F, Olmière C, Baudouin C, Buffault J, Mélik Parsadaniantz S. Evaluation of Rho kinase inhibitor effects on neuroprotection and neuroinflammation in an ex-vivo retinal explant model. Acta Neuropathol Commun. 2024 Sep 14;12(1):150. doi: 10.1186/s40478-024-01859-z. PMID: 39300576. 2: Halilovic M, Abdelsalam M, Zabkiewicz J, Lazenby M, Alvares C, Schmidt M, Brenner W, Najafi S, Oehme I, Hieber C, Zeyn Y, Bros M, Sippl W, Krämer OH. Selective degradation of mutant FMS-like tyrosine kinase-3 requires BIM- dependent depletion of heat shock proteins. Leukemia. 2024 Sep 17. doi: 10.1038/s41375-024-02405-5. Epub ahead of print. PMID: 39300221. 3: Fan J, Yang T, Wang H, Zhang H, Zhang W, Ji M, Miao J. A Self-Supervised Equivariant Refinement Classification Network for Diabetic Retinopathy Classification. J Imaging Inform Med. 2024 Sep 19. doi: 10.1007/s10278-024-01270-z. Epub ahead of print. PMID: 39299958. 4: Sozen-Delil FI, Comba OB, Ucar G. Evaluation of insomnia effect on ganglion cell complex, middle retina, and choroid. Int Ophthalmol. 2024 Sep 19;44(1):381. doi: 10.1007/s10792-024-03303-6. PMID: 39299944. 5: Yap A, Kaur D, Muttaiyah S, Welch S, Lightman S, Tomkins-Netzer O, Niederer RL. Impact of microorganism virulence on endophthalmitis outcomes. Br J Ophthalmol. 2024 Sep 18:bjo-2024-325605. doi: 10.1136/bjo-2024-325605. Epub ahead of print. PMID: 39299710. 6: Teng RW, Nguyen MTB, Hunter DG, Altschwager P. Intravenous fluorescein overdose in a child undergoing fluorescein angiography. J AAPOS. 2024 Sep 17:103996. doi: 10.1016/j.jaapos.2024.103996. Epub ahead of print. PMID: 39299511. 7: Kim A, Ding X, Miller JB. Ultra-widefield Swept-Source OCT Angiography vs. Ultra-widefield Fluorescein Angiography in Diabetic Retinopathy. Am J Ophthalmol. 2024 Sep 17:S0002-9394(24)00419-7. doi: 10.1016/j.ajo.2024.09.002. Epub ahead of print. PMID: 39299476. 8: Horvat Bröcker A, Reinhard J, Illes S, Paech T, Zoidl G, Harroch S, Distler C, Knyazev P, Ullrich A, Faissner A. Corrigendum to "Receptor protein tyrosine phosphatases are expressed by cycling retinal progenitor cells and involved in neuronal development of mouse retina" [Neuroscience 152(3) (2008) 618-645]. Neuroscience. 2024 Sep 16:S0306-4522(24)00473-1. doi: 10.1016/j.neuroscience.2024.09.021. Epub ahead of print. Erratum for: Neuroscience. 2008 Mar 27;152(3):618-45. doi: 10.1016/j.neuroscience.2008.01.016. PMID: 39299298. 9: AlQahtani GMS, Alkatan HM, AlMesfer S, Elkhamary S, Maktabi AMY. A case of retinoblastoma masquerading as endophthalmitis: Unusual presentation and clinicopathological correlation. Int J Surg Case Rep. 2024 Sep 10;123:110263. doi: 10.1016/j.ijscr.2024.110263. Epub ahead of print. PMID: 39299200. 10: Ekong F, Yu Y, Patamia RA, Sarpong K, Ukwuoma CC, Ukot AR, Cai J. RetVes segmentation: A pseudo-labeling and feature knowledge distillation optimization technique for retinal vessel channel enhancement. Comput Biol Med. 2024 Sep 18;182:109150. doi: 10.1016/j.compbiomed.2024.109150. Epub ahead of print. PMID: 39298884. 11: Caddy HT, Fujino M, Vahabli E, Voigt V, Kelsey LJ, Dilley RJ, Carvalho LS, Takahashi S, Green DJ, Doyle BJ. Simulation of murine retinal hemodynamics in response to tail suspension. Comput Biol Med. 2024 Sep 18;182:109148. doi: 10.1016/j.compbiomed.2024.109148. Epub ahead of print. PMID: 39298883. 12: Lakshmi Marella B, Conway ML, Vaddavalli PK, Suttle CM, Bharadwaj SR. Optical phase nullification partially restores visual and stereo acuity lost to simulated blur from higher-order wavefront aberrations of keratoconic eyes. Vision Res. 2024 Sep 18;224:108486. doi: 10.1016/j.visres.2024.108486. Epub ahead of print. PMID: 39298859. 13: Rabelo IA, Soares MC, Torigoe AMS. Profile of patients treated with intravitreal antiangiogenics in a Brazilian public service with high level of complexity. Arq Bras Oftalmol. 2023 Apr 17;87(5):e20220119. doi: 10.5935/0004-2749.2022-0119. PMID: 39298727. 14: Meşen S, Batur M, Ozer MD. A novel spot mutation leading to sialidosis type 1-myoclonus syndrome and optical coherence tomography findings. Arq Bras Oftalmol. 2023 Apr 3;87(5):e20220069. doi: 10.5935/0004-2749.2022-0069. PMID: 39298726. 15: Fernández-Berdasco K, Galvez-Olortegui J, Guillén-Lozada SP, González NG, Castro-Navarro J. PRPH2 mutation c.582-1G>A causing adult-onset macular dystrophy with a benign concentric annular macular dystrophy phenotype in a family. Arq Bras Oftalmol. 2023 Apr 3;87(5):e20210478. doi: 10.5935/0004-2749.2021-0478. PMID: 39298723. 16: Rodrigues Neto TDS, Silva Neto EDD, Higashi AH, Megnis BP, Haddad MAO, Monteiro MLR, Zacharias LC. Normative data for macular perimetry using the MP-3 microperimeter in healthy individuals. Arq Bras Oftalmol. 2023 Apr 3;87(5):e20210472. doi: 10.5935/0004-2749.2021-0472. PMID: 39298722. 17: Li W, He S, Tan J, Li N, Zhao C, Wang X, Zhang Z, Liu J, Huang J, Li X, Zhou Q, Hu K, Yang P, Hou S. Transcription factor EGR2 alleviates autoimmune uveitis via activation of GDF15 to modulate the retinal microglial phenotype. Proc Natl Acad Sci U S A. 2024 Sep 24;121(39):e2316161121. doi: 10.1073/pnas.2316161121. Epub 2024 Sep 19. PMID: 39298490. 18: Hassan T, Raja H, Belwafi K, Akcay S, Jleli M, Samet B, Werghi N, Yousaf J, Ghazal M. A Vision Language Correlation Framework for Screening Disabled Retina. IEEE J Biomed Health Inform. 2024 Sep 19;PP. doi: 10.1109/JBHI.2024.3462653. Epub ahead of print. PMID: 39298306. 19: Prieto-López L, Pereiro X, Vecino E. The mechanics of the retina: Müller glia role on retinal extracellular matrix and modelling. Front Med (Lausanne). 2024 Sep 4;11:1393057. doi: 10.3389/fmed.2024.1393057. PMID: 39296899; PMCID: PMC11410058. 20: Wu YX, Yin S, Song SS, Liu X, Deng YX, Lu XJ. Retinal ischemia-reperfusion injury and pretreatment with Lycium barbarum glycopeptide. Int J Ophthalmol. 2024 Sep 18;17(9):1599-1605. doi: 10.18240/ijo.2024.09.04. PMID: 39296572; PMCID: PMC11367443.