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Merck

R2500

Sigma-Aldrich

all trans-Retinal

powder, ≥98%

Sinónimos:

Vitamin A aldehyde

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About This Item

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

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biological source

synthetic (organic)

Quality Level

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

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D0531F9551F3651
color

yellow to orange

color

yellow to orange

color

yellow to orange

color

yellow to orange

fluorescence

λex 492 nm; λem 515 nm (Mercaptoethanol adduct), λex 493 nm; λem 522 nm (pH 9.2)

fluorescence

λex 495 nm; λem 516 nm

fluorescence

λex 511-519 nm

fluorescence

-

solubility

DMSO: 5 mg/mL

solubility

methanol: 20 mg/mL, clear to slightly hazy, yellow to orange

solubility

DMSO or DMF: soluble

solubility

acetone: 1 mg/mL, clear, light yellow to yellow

application(s)

diagnostic assay manufacturing
hematology
histology

application(s)

diagnostic assay manufacturing
hematology
histology

application(s)

diagnostic assay manufacturing
hematology
histology

application(s)

diagnostic assay manufacturing
hematology
histology

form

powder

form

powder

form

powder

form

powder

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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Certificados de análisis (COA)

Lot/Batch Number

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Encuentre la documentación para los productos que ha comprado recientemente en la Biblioteca de documentos.

Visite la Librería de documentos

Hai Li et al.
The Journal of biological chemistry, 291(49), 25319-25325 (2016-10-30)
Natural anion channelrhodopsins (ACRs) recently discovered in cryptophyte algae are the most active rhodopsin channels known. They are of interest both because of their unique natural function of light-gated chloride conductance and because of their unprecedented efficiency of membrane hyperpolarization
Optogenetic control of fly optomotor responses
Haikala V, et al.
The Journal of Neuroscience, 33(34), 13927-13934 (2013)
Juan Antonio Sánchez-Alcañiz et al.
Nature communications, 9(1), 4252-4252 (2018-10-14)
Through analysis of the Drosophila ionotropic receptors (IRs), a family of variant ionotropic glutamate receptors, we reveal that most IRs are expressed in peripheral neuron populations in diverse gustatory organs in larvae and adults. We characterise IR56d, which defines two
Advanced Nutrition Micronutrients, 23-23 (2019)
Smoking-induced upregulation of AKR1B10 expression in the airway epithelium of healthy individuals
Wang R, et al.
Chest, 138(6), 1402-1410 (2010)

Artículos

All-trans retinoic acid (RA, ATRA) is a pleiotropic activation factor that regulates genes associated with normal vertebrate cellular processes such as cell differentiation, cell proliferation, apoptosis, and embryonic development.

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