This product is soluble in 95% Ethanol at 2.7mg/mL and in absolute ethanol at 3mg/mL. Please see the link below to review the product datasheet for additional solvents and solution storage information:
https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/product/documents/231/812/r2625pis.pdf
R2625
Retinoic acid
≥98% (HPLC), powder, RAR and RXR ligand
Synonym(s):
ATRA, Tretinoin, Vitamin A acid, all-trans-Retinoic acid
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50 MG
€58.40
100 MG
€98.30
500 MG
€224.00
1 G
€403.00
5 G
€854.00
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50 MG
€58.40
100 MG
€98.30
500 MG
€224.00
1 G
€403.00
5 G
€854.00
About This Item
Empirical Formula (Hill Notation):
C20H28O2
CAS Number:
Molecular Weight:
300.44
Beilstein:
2057223
EC Number:
MDL number:
UNSPSC Code:
12352106
PubChem Substance ID:
NACRES:
NA.77
Recommended Products
Product Name
Retinoic acid, ≥98% (HPLC), powder
biological source
synthetic (organic)
Quality Level
Assay
≥98% (HPLC)
form
powder
technique(s)
cell culture | mammalian: suitable
color
yellow
mp
180-181 °C (lit.)
solubility
chloroform: 50 mg/mL
storage temp.
−20°C
SMILES string
CC1=C(\C=C\C(C)=C\C=C\C(C)=C\C(O)=O)C(C)(C)CCC1
InChI
1S/C20H28O2/c1-15(8-6-9-16(2)14-19(21)22)11-12-18-17(3)10-7-13-20(18,4)5/h6,8-9,11-12,14H,7,10,13H2,1-5H3,(H,21,22)/b9-6+,12-11+,15-8+,16-14+
InChI key
SHGAZHPCJJPHSC-YCNIQYBTSA-N
Gene Information
human ... RARA(5914) , RARB(5915) , RARG(5916) , RXRA(6256) , RXRB(6257) , RXRG(6258)
mouse ... Rara(19401) , Rarb(218772) , Rarg(19411) , Rxrb(20182)
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General description
Retinoic acid (RA), a retinoid, exerts a broad range of biological effects. It plays a role in regulating cellular differentiation and proliferation in both normal and transformed cells, potentially influencing oncogenes.[1] All-trans retinoic acid (ATRA) is regarded as the most pertinent and functionally active metabolite of Vitamin-A.[2] RA may serve as a type of signal molecule through a nuclear receptor to regulate regional differentiation in the central nervous system. Moreover, at a concentration of 1 nM (with maximal differentiation at 1 µM), RA induces morphological and functional terminal differentiation in a cell line of human promyelocyte leukemia, indicating its potential involvement in the differentiation of specific hematopoietic cells. Additionally, RA can indirectly impact neuronal differentiation by modifying the expression of neuronal cell surface receptors to peptide growth factors.[3]
Furthermore, RA and other retinoids can also inhibit cellular proliferation and stimulate tyrosinase activity in a human melanoma cell line,[4] while also inhibiting cell-substrate adhesion and motility in melanocytes. ATRA plays a vital role in the formation of the mammalian vascular system. Specifically, it regulates endothelial cell proliferation and vascular remodeling throughout tissue angiogenesis.[2]
Furthermore, RA and other retinoids can also inhibit cellular proliferation and stimulate tyrosinase activity in a human melanoma cell line,[4] while also inhibiting cell-substrate adhesion and motility in melanocytes. ATRA plays a vital role in the formation of the mammalian vascular system. Specifically, it regulates endothelial cell proliferation and vascular remodeling throughout tissue angiogenesis.[2]
Application
- Retinoic acid (RA) has been used for the differentiation of embryonic stem cells into motor neurons.[5]
- It has been used for the differentiation of Xenopus ectoderm into pancreas.[6]
- It has also been used to study epigenetic regulation by RARα (retinoic acid receptor α).[7]
- It has been used to study RA signaling of prospermatogonia transition into spermatogonia.[8]
Biochem/physiol Actions
all−trans−Retinoic acid (ATRA) is a ligand for both the retinoic acid receptor (RAR) and the retinoid X receptor (RXR). The bound RAR and RXR act as transcription factors that regulate the growth and differentiation of both normal and malignant cells. Cytochromes P450 (CYPs) catalyze the 4-hydroxylation of ATRA. Retinoic acid primes embryonic stem cells to become neurons.
Ligand for both the retinoic acid receptor (RAR) and the retinoid X receptor (RXR); primes embryonic stem cells to become neurons.
Features and Benefits
This compound is featured on the Nuclear Receptors (Non-Steroids) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
Signal Word
Danger
Hazard Statements
Precautionary Statements
Hazard Classifications
Acute Tox. 4 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Repr. 1B - Skin Irrit. 2
Storage Class Code
6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
WGK
WGK 2
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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Articles
Derivation and characterization of functional human neural stem cell derived oligodendrocyte progenitor cells (OPCs) that efficiently myelinate primary neurons in culture.
Protocols
Step-by-step culture protocols for neural stem cell culture including NSC isolation, expansion, differentiation and characterization.
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Is it possible to dilute RA in alcohol?
1 answer-
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Can I dissolve retinoic acid in PEG 1500?
1 answer-
This compound has not been tested for solubility in PEG 1500. Various sources report that retinoic acid is slightly soluble in PEG 400. This information has not been validated. Other solvents include DMSO at 25 mg/mL, ethanol at 10 mg/mL, DMF at 20 mg/mL, chloroform at 40 mg/mL, and acetone at 30 mg/mL. Please see the link below to review the product datasheet which includes additional information on solubility and stability:
https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/product/documents/231/812/r2625pis.pdfHelpful?
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After dissolving the Retinoic acid in DMSO to create a 20mM stock concentration, I diluted it 1,000 times to achieve a final concentration of 20μM. Crystals have formed in the cell culture dishes where I added this solution but not in the DMSO vehicle dishes. Could there be an issue with this lot, or are there other reasons why crystals are forming?
1 answer-
The product R2625 is soluble at around 40 mg/ml in DMSO, yielding a clear solution. Although the stock seems fine, adding the DMSO solution to the media causes crystals to form. This is common when diluting a high-concentration stock made in organic solvents into aqueous media. To address this, try reducing the stock solution to lower concentrations in DMSO multiple times before adding it to the media to ensure an adequate organic environment around the product. There is nothing wrong with the product itself.
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Can I reconstitute retinoic acid in water instead of chlorofrom? What is its solubility in water?
1 answer-
The solubility of each Lot of Retinoic Acid is tested in chloroform as shown on the specification sheet.
https://www.sigmaaldrich.com/specification-sheets/150/073/R2625-BULK________SIGMA____.pdfThe Product Information Sheet provides additional solvents, however, water is not recommended:
"RA is more sensitive to light, heat, and air in solution. It is practically insoluble in water; slightly soluble in alcohol and chloroform, sparingly soluble in ether, and soluble in methylene chloride. RA is soluble at about 40 mg/ml in DMSO and at about 2.7 mg/ml in 95% ethanol (vortexing may be needed). "
https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/product/documents/231/812/r2625pis.pdfHelpful?
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How long can you store RA in solution?
1 answer-
Stock solutions can be stored at -70 °C for up to two weeks.
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I bought 1 gram. How do I crush the vial? I can't break it with force.
1 answer-
The 1 G pack size is packaged in a 5 mL glass ampule. This packaging may be opened using ampule breakers. Kindly review the following links: https://www.sigmaaldrich.com/US/en/product/aldrich/z693847 and https://www.sigmaaldrich.com/US/en/product/aldrich/z122890.
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Could we reconstitute Retinoic Acid 30mM in DMSO instead of chloroform?
1 answer-
Yes, this product is soluble in DMSO at 25 mg/mL.
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What is the Department of Transportation shipping information for this product?
1 answer-
Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product.
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What are the I.U. for Product R2625, Retinoic acid?
1 answer-
This product is not characterized by the activity in I.U. The purity specification, however, is not less than 98% by HPLC.
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Why is Product R2625, Retinoic acid not shipped on dry ice?
1 answer-
Dry ice is not necessary for shipment, since Product No. R2625 is stable to ship at ambient temperature for up to two weeks. Once received, it should be stored at -20°C.
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