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
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50 MG
$100.00
100 MG
$123.00
500 MG
$284.00
1 G
$579.00
5 G
$2,300.00
About This Item
经验公式（希尔记法）:
C20H28O2
CAS号:
分子量:
300.44
Beilstein:
2057223
EC號碼:
MDL號碼:
分類程式碼代碼:
12352106
PubChem物質ID:
NACRES:
NA.77
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产品名称
视黄酸, ≥98% (HPLC), powder
生物源
synthetic (organic)
品質等級
化驗
≥98% (HPLC)
形狀
powder
技術
cell culture | mammalian: suitable
顏色
yellow
mp
180-181 °C (lit.)
溶解度
chloroform: 50 mg/mL
儲存溫度
−20°C
SMILES 字串
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 密鑰
SHGAZHPCJJPHSC-YCNIQYBTSA-N
基因資訊
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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一般說明
视黄酸(RA)是一种类视黄醇，具有广泛的生物学作用。可调节正常和转化细胞的分化和增殖，可能会影响癌基因。[1]全反式视黄酸(ATRA)是维生素A最直接相关的活性代谢产品。[2]视黄酸可作为一种信号分子，经由核受体调节中枢神经系统的区域分化。1 nm浓度（1 µM带来最大分化）的视黄酸可诱导一种人早幼粒细胞白血病细胞系形态和功能上的终末分化，代表其可能参与特定造血细胞的分化。视黄酸还可通过调节神经元细胞表面肽生长因子受体的表达，间接影响神经元分化。[3]
此外，视黄酸等类视黄醇可抑制人黑素瘤细胞的增殖并刺激酪氨酸酶活性，[4]还抑制黑色素细胞的细胞基底黏附和迁移。ATRA在哺乳动物血管系统形成中起重要作用，尤其是可以调节组织血管生成过程中的内皮细胞增殖和血管重塑。[2]
此外，视黄酸等类视黄醇可抑制人黑素瘤细胞的增殖并刺激酪氨酸酶活性，[4]还抑制黑色素细胞的细胞基底黏附和迁移。ATRA在哺乳动物血管系统形成中起重要作用，尤其是可以调节组织血管生成过程中的内皮细胞增殖和血管重塑。[2]
應用
生化／生理作用
全−反式−视黄酸（ATRA）是视黄酸受体（RAR）和视黄醇类 X 受体（RXR）的配体。所结合的RAR和RXR可作为调节正常细胞和恶性细胞的生长和分化的转录因子。细胞色素P450（CYP）可催化ATRA的4-羟基化。视黄酸可使胚胎干细胞成为神经元。
视黄酸受体（RAR）和类视黄醇X受体（RXR）的配体; 引发胚胎干细胞成为神经元。
特點和優勢
该化合物在受体分类和信号转导手册中 核受体（非甾体化合物） 页面中进行了详细介绍。欲浏览其他手册页面，请 点击这里。
訊號詞
Danger
危險分類
Acute Tox. 4 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Repr. 1B - Skin Irrit. 2
儲存類別代碼
6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
水污染物質分類（WGK）
WGK 2
閃點（°F）
Not applicable
閃點（°C）
Not applicable
個人防護裝備
dust mask type N95 (US), Eyeshields, Gloves
历史批次信息供参考:
分析证书(COA)
Lot/Batch Number
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商品
Derivation and characterization of functional human neural stem cell derived oligodendrocyte progenitor cells (OPCs) that efficiently myelinate primary neurons in culture.
实验方案
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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