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Merck

R2500

all trans-Retinal

powder, ≥98%

Sinónimos:

Vitamin A aldehyde

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Fórmula empírica (notación de Hill):
C20H28O
Número CAS:
Peso molecular:
284.44
NACRES:
NA.79
PubChem Substance ID:
UNSPSC Code:
12352205
MDL number:
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Nombre del producto

all trans-Retinal, powder, ≥98%

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 string

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

InChI key

NCYCYZXNIZJOKI-OVSJKPMPSA-N

biological source

synthetic (organic)

assay

≥98%

form

powder

technique(s)

HPLC: suitable

color

yellow

mp

62-64 °C

shipped in

dry ice

storage temp.

−20°C

Quality Level

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Application

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

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.

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.

Packaging

Sealed ampule.

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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
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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.
Optogenetic and pharmacologic dissection of feedforward inhibition in Drosophila motion vision
Mauss AS, et al.
The Journal of Neuroscience, 34(6), 2254-2263 (2014)
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ACS omega, 5(5), 2397-2405 (2020-02-18)
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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

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