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trans-Retinoic Acid

trans-Retinoic Acid

Product ID R1780
Cas No. 302-79-4
Purity ≥98%
Product Unit SizeCostQuantityStock
500 mg $85.20 In stock
1 g $141.80 In stock
5 g $425.70 In stock
Bulk Quote

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Description

Trans-retinoic acid (RA) is an activator of the retinoic acid receptor (RAR) that exhibits anti-fibrotic, antiviral, antibacterial, immunomodulatory, and anticancer chemotherapeutic activities. RA is a vitamin A carboxylic acid that is clinically used to treat acne vulgaris, keratosis pilaris, and acute promyelocytic leukemia (APL). In vivo, RA inhibits fibroblast proliferation and scar formation and decreases levels of TGF-β1, IL-6, and NF-κB. This compound also induces expression of IFNα in cells infected with enterovirus 71, decreasing viral infectivity. In subjects with APL, retinoic acid forces promyelocytes to differentiate into normal blood cells. In cutaneous squamous cell carcinoma cells, RA induces G1 phase cell cycle arrest, increases expression of p21 and p27, decreases expression of cyclin D1/CDK4 and cyclin E/CDK2, and induces apoptosis. RA decreases cellular cholesterol and inhibits Mycobacterium in an NPC2-dependent manner. This compound also induces expression of hedgehog (Hh) signaling receptor Patched 1, inhibiting Hh signaling.

Product Info

Cas No.

302-79-4

Purity

≥98%

Formula

C20H28O2

Formula Wt.

300.44

Chemical Name

(all-E)-3,7-Dimethyl-9-(2,6,6-trimethyl- 1-cyclo-hexen- 1-yl)-2,4,6,8-nonatetraenoic acid

IUPAC Name

(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6, 8-tetraenoic acid

Synonym

Retinoic acid, Vitamin A acid, tretinoin, Aberel, Avita, Eudyna, Kerlocal, Renova, Retin-A, Vesanoid

Melting Point

180-182°C

Solubility

Soluble in DMSO. Slightly soluble in polyethylene glycol, octanol or ethanol. Practically insoluble in water, mineral oil or glycerin.

Appearance

Yellow/slight orange crystal powder

Shipping and Storage

Store Temp

-20°C

Ship Temp

Ambient

Downloads

MSDS

R1780 MSDS PDF

Info Sheet

R1780 Info Sheet PDF

References

Chen S, Yang Y, Xu J, et al. Effect of all-trans-retinoic acid on enterovirus 71 infection in vitro. Br J Nutr. 2014 May;111(9):1586-93. PMID: 24495389.

Zhang ML, Tao Y, Zhou WQ, et al. All-trans retinoic acid induces cell-cycle arrest in human cutaneous squamous carcinoma cells by inhibiting the mitogen-activated protein kinase-activated protein 1 pathway. Clin Exp Dermatol. 2014 Apr;39(3):354-60. PMID: 24635079.

Busch AM, Galimberti F, Nehls KE, et al. All-trans-retinoic acid antagonizes the Hedgehog pathway by inducing patched. Cancer Biol Ther. 2014 Apr;15(4):463-72. PMID: 24496080.

Zhang C, Kong X, Ning G, et al. All-trans retinoic acid prevents epidural fibrosis through NF-κB signaling pathway in post-laminectomy rats. Neuropharmacology. 2014 Apr;79:275-81. PMID: 24316159.

Wheelwright M, Kim EW, Inkeles MS, et al. All-trans retinoic acid-triggered antimicrobial activity against Mycobacterium tuberculosis is dependent on NPC2. J Immunol. 2014 Mar 1;192(5):2280-90. PMID: 24501203.

Zhu YF, Hu JZ, Zhao PN, et al. All-transretinoic acid regulates Th1/Th2 balance in CD4+ T cells when GATA-3 is deficient. Biomed Environ Sci. 2013 Sep;26(9):774-7. PMID: 24099613.

Chomienne C, Ballerini P, Balitrand N, et al. All-trans retinoic acid in acute promyelocytic leukemias. II. In vitro studies: structure-function relationship. Blood. 1990 Nov 1;76(9):1710-7. PMID: 2224120.

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