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R2500

Sigma-Aldrich

all trans-Retinal

powder, ≥98%

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Synonym(s):
Vitamin A aldehyde
Empirical Formula (Hill Notation):
C20H28O
CAS Number:
Molecular Weight:
284.44
MDL number:
PubChem Substance ID:
NACRES:
NA.79

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

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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1 of 4

This Item
R575495144R7632
all trans-Retinal powder, ≥98%

Sigma-Aldrich

R2500

all trans-Retinal

-
9-cis-Retinal vitamin A analog

Sigma-Aldrich

R5754

9-cis-Retinal

-
Retinol BioXtra, ≥97.5% (HPLC), ~3100 U/mg

Sigma-Aldrich

95144

Retinol

Premium Grade
Retinol synthetic, ≥95% (HPLC), (Powder or Powder with Lumps)

Sigma-Aldrich

R7632

Retinol

-
assay

≥98%

assay

≥95% (HPLC)

assay

≥97.5% (HPLC)

assay

≥95% (HPLC)

form

powder

form

powder

form

(Powder or Powder with Lumps)

form

(Powder or Powder with Lumps)

technique(s)

HPLC: suitable

technique(s)

HPLC: suitable

technique(s)

-

technique(s)

HPLC: suitable

color

yellow

color

yellow to yellow-orange

color

faint yellow to very dark yellow

color

yellow to very dark yellow, to Very Dark Orange

mp

62-64 °C

mp

56-58 °C (lit.)

mp

56-61 °C, 61-63 °C (lit.)

mp

61-63 °C (lit.)

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.

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.

Packaging

Sealed ampule.

Certificates of Analysis (COA)

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25G
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Yasushi Imamoto et al.
Biochimica et biophysica acta, 1837(5), 664-673 (2013-09-12)
Cone visual pigments are visual opsins that are present in vertebrate cone photoreceptor cells and act as photoreceptor molecules responsible for photopic vision. Like the rod visual pigment rhodopsin, which is responsible for scotopic vision, cone visual pigments contain the
Jihye Yeon et al.
PLoS biology, 16(6), e2004929-e2004929 (2018-06-09)
Animal locomotion is mediated by a sensory system referred to as proprioception. Defects in the proprioceptive coordination of locomotion result in uncontrolled and inefficient movements. However, the molecular mechanisms underlying proprioception are not fully understood. Here, we identify two transient
Smoking-induced upregulation of AKR1B10 expression in the airway epithelium of healthy individuals
Wang R, et al.
Chest, 138(6), 1402-1410 (2010)
Optogenetic control of fly optomotor responses
Haikala V, et al.
The Journal of Neuroscience, 33(34), 13927-13934 (2013)
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

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