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R2500

Sigma-Aldrich

all trans-Retinal

powder, ≥98%

Synonym(s):

Vitamin A aldehyde

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About This Item

Empirical Formula (Hill Notation):
C20H28O
CAS Number:
116-31-4
Molecular Weight:
284.44
MDL number:
MFCD00001550
UNSPSC Code:
12352205
PubChem Substance ID:
24899355
NACRES:
NA.79
Pricing and availability is not currently available.

biological source

synthetic (organic)

Quality Level

200

Assay

≥98%

form

powder

technique(s)

HPLC: suitable

color

yellow

mp

62-64 °C

shipped in

dry ice

storage temp.

−20°C

SMILES string

[H]C(=O)\C=C(C)\C=C\C=C(C)\C=C\C1=C(C)CCCC1(C)C

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+

InChI key

NCYCYZXNIZJOKI-OVSJKPMPSA-N

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General description

All trans-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.[1]

Application

All trans-Retinal has been used:
  • in optogenetic experiments[2]
  • in electrophysiological experiment[3]
  • to study the effect of AKR1B10 (aldo-keto reductase (AKR) superfamily member) on the conversion of retinal to retinol in the airway epithelium[4]
  • in decidual transformation of human endometrial stromal cells[5]

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.

Packaging

Sealed ampule.

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Certificates of Analysis (COA)

Lot/Batch Number
0000413912
0000413910
0000413909
0000409393
0000409390

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Tretinoin United States Pharmacopeia (USP) Reference Standard

USP

1674004

Tretinoin

Tretinoin European Pharmacopoeia (EP) Reference Standard

T1850000

Tretinoin

Retinol solution 100 μg/mL ± 25% (Refer to COA) (Ethanol with 0.1% (w/v) BHT), ampule of 1 mL, reference material, Cerilliant®

Supelco

V-011

Retinol solution

Retinyl acetate synthetic, crystalline solid or supercooled liquid

Sigma-Aldrich

R4632

Retinyl acetate

Optogenetic and pharmacologic dissection of feedforward inhibition in Drosophila motion vision
Mauss AS, et al.
The Journal of Neuroscience, 34(6), 2254-2263 (2014)
Lieuwe Biewenga et al.
ACS omega, 5(5), 2397-2405 (2020-02-18)
The efficient engineering of iminium biocatalysis has drawn considerable attention, with many applications in pharmaceutical synthesis. Here, we report a tailor-made iminium-activated colorimetric "turn-on" probe, specifically designed as a prescreening tool to facilitate engineering of iminium biocatalysis. Upon complexation of
Ye Zhang et al.
Nature communications, 10(1), 1560-1560 (2019-04-07)
In the Drosophila antenna, different subtypes of olfactory receptor neurons (ORNs) housed in the same sensory hair (sensillum) can inhibit each other non-synaptically. However, the mechanisms underlying this underexplored form of lateral inhibition remain unclear. Here we use recordings from
Alexandria H Jaeger et al.
eLife, 7 (2018-10-12)
Each taste modality is generally encoded by a single, molecularly defined, population of sensory cells. However, salt stimulates multiple taste pathways in mammals and insects, suggesting a more complex code for salt taste. Here, we examine salt coding in Drosophila.
Shiho Kawamura et al.
Structure (London, England : 1993), 21(3), 426-437 (2013-02-26)
Rhodopsin, the photoreceptor pigment of the retina, initiates vision upon photon capture by its covalently linked chromophore 11-cis-retinal. In the absence of light, the chromophore serves as an inverse agonist locking the receptor in the inactive dark state. In the
View All Related Papers

Questions

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  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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