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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:
116-31-4
Peso molecular:
284.44
Número MDL:
MFCD00001550
Código UNSPSC:
12352205
ID de la sustancia en PubChem:
24899355
NACRES:
NA.79
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origen biológico

synthetic (organic)

Nivel de calidad

200

Ensayo

≥98%

Formulario

powder

técnicas

HPLC: suitable

color

yellow

mp

62-64 °C

Condiciones de envío

dry ice

temp. de almacenamiento

−20°C

cadena SMILES

[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+

Clave InChI

NCYCYZXNIZJOKI-OVSJKPMPSA-N

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Descripción general

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]

Aplicación

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]

Acciones bioquímicas o fisiológicas

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.

Envase

Sealed ampule.

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Certificados de análisis (COA)

Lot/Batch Number
0000413912
0000413910
0000413909
0000409393
0000409390

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Ácido retinoico United States Pharmacopeia (USP) Reference Standard

USP

1674004

Ácido retinoico

Ácido retinoico European Pharmacopoeia (EP) Reference Standard

T1850000

Ácido retinoico

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

Acetato de retinil synthetic, crystalline solid or supercooled liquid

Sigma-Aldrich

R4632

Acetato de retinil

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
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
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
Smoking-induced upregulation of AKR1B10 expression in the airway epithelium of healthy individuals
Wang R, et al.
Chest, 138(6), 1402-1410 (2010)
Advanced Nutrition Micronutrients, 23-23 (2019)
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Questions

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  1. 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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  2. 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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