This product is packaged as a neat oil in an all-glass ampule, and it would be best to keep it in that ampule until it is time to use the product, to prevent oxidation. Once the ampule is broken open, manipulations (transfer, dissolving, making aliquots) should be done quickly. Either plastic or glass pipettes and vials can be used.
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About This Item
经验公式（希尔记法）:
C22H32O2
CAS号:
分子量:
328.49
Beilstein:
1715505
MDL编号:
UNSPSC代码:
12352211
PubChem化学物质编号:
NACRES:
NA.25
价格与库存信息目前不能提供
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生物来源
algae
方案
≥98%
表单
liquid
官能团
carboxylic acid
脂质类型
omega FAs
运输
dry ice
储存温度
−20°C
SMILES字符串
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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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)
历史批次信息供参考:
分析证书(COA)
Lot/Batch Number
其他客户在看
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
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
J L Tremoleda et al.
European journal of nuclear medicine and molecular imaging, 43(9), 1710-1722 (2016-05-08)
Traumatic spinal cord injury (SCI) is a devastating condition which affects millions of people worldwide causing major disability and substantial socioeconomic burden. There are currently no effective treatments. Modulating the neuroinflammatory (NI) response after SCI has evolved as a major
Guang Yang et al.
Journal of cellular and molecular medicine, 19(10), 2413-2422 (2015-07-16)
Previous work from both our lab and others have indicated that exposure to 50 Hz magnetic fields (ELF-MF) was able to modify ion channel functions. However, very few studies have investigated the effects of MF on γ-aminobutyric acid (GABA) type
商品
Lipid Induced Insulin Resistance
脂肪组织中的胰岛素耐受性减少了循环游离脂肪酸的摄入，并增加了脂肪酶对储存甘油三酯的水解。了解与胰岛素耐受性相关的激素、细胞因子和脂肪因子。
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Can I use regular tips and vials instead of glass?
1 answer-
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How is shipping temperature determined? And how is it related to the product storage temperature?
1 answer-
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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How can I determine the shelf life / expiration / retest date of this product?
1 answer-
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.pdfHelpful?
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Is Product D2534, cis-4,7,10,13,16,19-Docosahexaenoic acid soluble in DMSO? If so, what is the solubility of the product in DMSO?
1 answer-
This product has not been tested for solubility in DMSO. However, various sources state this product can be solubilized in DMSO at a concentration of 100 mM.
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What is the best way to prepare a solution of Product D2534, cis-4,7,10,13,16,19-Docosahexaenoic acid?
1 answer-
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.
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Are all of the double bonds in the Product D2534, cis-4,7,10,13,16,19-Docosahexaenoic acid, in the cis-configuration?
1 answer-
Yes, this product's double bond configuration is cis.
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After I prepare a solution of Product D2534, cis-4,7,10,13,16,19-Docosahexaenoic acid, in ethanol, how should it be stored?
1 answer-
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.
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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?
1 answer-
D2534 is not a solution; it is a neat oil. The density of D2534 is approximately 0.95 g/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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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?
1 answer-
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).
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