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D2534

Sigma-Aldrich

顺式 -4,7,10,13,16,19-二十二碳六烯酸标准液

≥98%

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别名:
DHA
经验公式（希尔记法）:
C22H32O2
CAS号:
6217-54-5
分子量:
328.49
Beilstein:
1715505
MDL编号:
MFCD00065722
PubChem化学物质编号:
24893696
NACRES:
NA.25

生物来源

algae

检测方案

≥98%

形式

liquid

官能团

carboxylic acid

lipid type

omega FAs

运输

dry ice

储存温度

−20°C

SMILES string

CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCC(O)=O

InChI

1S/C22H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24/h3-4,6-7,9-10,12-13,15-16,18-19H,2,5,8,11,14,17,20-21H2,1H3,(H,23,24)/b4-3-,7-6-,10-9-,13-12-,16-15-,19-18-

InChI key

MBMBGCFOFBJSGT-KUBAVDMBSA-N

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相关类别

一般描述

二十二碳六烯酸（DHA）大量存在于大脑中。
二十二碳六烯酸（DHA）是一种含22个碳和6个双键的ω-3多不饱和脂肪酸，其第一个双键位于甲基末端的第3位（22：6 n-3）。 它是脂质膜和髓鞘的组分。

应用

cis-4,7,10,13,16,19-二十二碳六烯酸已用于：
  • 用作杜氏改良Eagle培养基（DMEM）的组分，用于培养细胞进行二十二碳六烯酸（DHA）处理
  • 研究其在分子和细胞水平上对人诱导多能干细胞（iPSC）衍生神经元的影响
  • MTT[3-(4,5-二甲基噻唑-2-基)-2,5-二苯基溴化四氮唑]试验，研究对3种人肝细胞癌（HCC）细胞系（HepG2、Hep3B、Huh7）的细胞毒性作用

生化/生理作用

二十二碳六烯酸（DHA）参与中枢神经系统的生长和生理活动。它可以调节成人神经发生和神经可塑性。DHA在胎儿大脑发育中起重要作用。它可能表现出抗氧化和抗炎的特性。DHA在细胞膜流动性的调节中起重要作用。它在几个大脑发育过程中起着至关重要的作用，包括神经递质释放、基因表达、髓鞘形成、神经炎症和神经元分化。DHA对几种癌症都有抗癌作用。
二十二碳六烯酸（DHA）还可用作前列腺素和类二十烷酸等信号传导分子的前体。

包装

安瓿瓶装。

储存分类代码

10 - Combustible liquids

WGK

WGK 3

闪点(°F)

143.6 °F - closed cup

闪点(°C)

62 °C - closed cup

个人防护装备

Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)

分析证书(COA)

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示例

T1503
货号
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25G
包装规格/数量

其它示例：

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1000309185

输入内容 1.000309185)

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  • 如果您查询到的批号为 TO09019TO 等，请输入去除前两位字母的批号：09019TO。

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索取COA

  1. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

  2. How do I get lot-specific information or a Certificate of Analysis?

    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

  3. Is Product D2534, cis-4,7,10,13,16,19-Docosahexaenoic acid, a solution? If so, what is the solvent? If not, what is the density?

    D2534 is not a solution; it is a neat oil. The density of D2534 is approximately 0.95 g/mL.

  4. What is the best way to prepare a solution of Product D2534, cis-4,7,10,13,16,19-Docosahexaenoic acid?

    D2534 is soluble in chloroform at a concentration of 50 mg/mL. For biological or biochemical applications, chloroform is probably not suitable. Information in our files indicates that the product would be expected to be soluble in 95% ethanol to at least 10 mg/mL.

  5. After I prepare a solution of Product D2534, cis-4,7,10,13,16,19-Docosahexaenoic acid, in ethanol, how should it be stored?

    The solution in ethanol would be unstable.  It is best to make solutions up fresh.  If this is not possible, divide the solution into aliquots and layer argon or nitrogen over the solution in each vial.  Also, the product may be packaged in ampules, or kept in a vial with a cap plug or vacuum seal and stored at -70 °C.  Any antioxidant such as BHT (di-tert-butyl hydroxytoluene) will aid in preventing oxidation of this product.  BHT would be one of the better antioxidants to use.  It can be used at 0.1% w/w or in the most extreme cases up to 1%.  The most important thing to do to prevent oxidation is to exclude oxygen from contacting the product.

  6. I know that Product D2534, cis-4,7,10,13,16,19-Docosahexaenoic acid, is very prone to oxidation. I would like to study the oxidation in detail. Do you have any references?

    A rapid method for studying the oxidation of fatty acids, including linoleic acid, eicosapentaenoic acid and docosahexaenoic acid, has been published. Boyd, L.C., et al., A rapid method for determining the oxidation of n-3 fatty acids. J. Am. Oil Chem. Soc., 69, 325-330 (1992).

  7. Are all of the double bonds in the Product D2534, cis-4,7,10,13,16,19-Docosahexaenoic acid, in the cis-configuration?

    Yes, this product's double bond configuration is cis.

  8. How do I find price and availability?

    There are several ways to find pricing and availability for our products. Once you log onto our website, you will find the price and availability displayed on the product detail page. You can contact any of our Customer Sales and Service offices to receive a quote.  USA customers:  1-800-325-3010 or view local office numbers.

  9. What is the Department of Transportation shipping information for this product?

    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. 

  10. My question is not addressed here, how can I contact Technical Service for assistance?

    Ask a Scientist here.

G Kargas et al.
Journal of chromatography, 526(2), 331-340 (1990-04-06)
A rapid, simple and highly sensitive reversed-phase high-performance liquid chromatographic method is described for the separation and quantitation of fatty acids in human serum using a very reactive fluorescent labeling reagent, 9-anthryldiazomethane. Quantitative esterification proceeds at room temperature without heat
Walter J Lukiw et al.
The Journal of clinical investigation, 115(10), 2774-2783 (2005-09-10)
Deficiency in docosahexaenoic acid (DHA), a brain-essential omega-3 fatty acid, is associated with cognitive decline. Here we report that, in cytokine-stressed human neural cells, DHA attenuates amyloid-beta (Abeta) secretion, an effect accompanied by the formation of NPD1, a novel, DHA-derived
M Martínez
Neurology, 40(8), 1292-1298 (1990-08-01)
In confirmation of previous findings, patients with Zellweger's syndrome had extremely low levels of docosahexaenoic acid (22:6 omega 3) in the brain, liver, and kidneys. The other product of delta 4 desaturation, 22:5 omega 6, was also very significantly decreased
Ana M Torres-Guzman et al.
Arthritis research & therapy, 16(2), R64-R64 (2014-03-13)
Clinical and preclinical studies have shown that supplementation with ω-3 polyunsaturated fatty acids (ω-3 PUFAs) reduce joint destruction and inflammation present in rheumatoid arthritis (RA). However, the effects of individual ω-3 PUFAs on chronic arthritic pain have not been evaluated
Eduardo Luiz Moreira et al.
Toxicological sciences : an official journal of the Society of Toxicology, 130(2), 373-382 (2012-08-21)
Methylmercury (MeHg) is an environmental pollutant that biomagnifies throughout the aquatic food chain, thus representing a toxicological concern for humans subsiding on fish for their dietary intake. Although the developing brain is considered the critical target organ of MeHg toxicity
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