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D2534

Acide cis-4,7,10,13,16,19-docosahexaénoïque

≥98%

Synonyme(s) :

DHA

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A propos de cet article

Formule empirique (notation de Hill) :
C22H32O2
Numéro CAS:
Poids moléculaire :
328.49
UNSPSC Code:
12352211
NACRES:
NA.25
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
1715505
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biological source

algae

Quality Level

assay

≥98%

functional group

carboxylic acid

lipid type

omega FAs

shipped in

dry ice

storage temp.

−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

General description

L'acide docosahexaénoïque (DHA) est présent en abondance dans le cerveau.
L'acide docosahexaénoïque (DHA) est un acide gras polyinsaturé oméga-3 à 22 carbones et six liaisons doubles (dont la première liaison double est en position trois par rapport à l'extrémité méthyle (22:6 n-3). C'est un constituant des membranes lipidiques et de la gaine de myéline.

Application

L'acide cis-4,7,10,13,16,19-docosahexaénoïque a été utilisé :
  • comme constituant d'un milieu de Eagle modifié par Dulbecco (DMEM) destiné à la culture de cellules pour appliquer un traitement à l'acide docosahexaénoïque (DHA).
  • pour étudier ses effets sur des cellules neuronales dérivées de cellules souches pluripotentes induites (CSPi) humaines à l'échelle moléculaire et cellulaire.
  • dans un test au MTT [bromure de 3-(4,5-diméthylthiazol-2-yl)-2,5-diphényl tétrazolium] pour étudier ses effets cytotoxiques sur trois lignées cellulaires de carcinome hépatocellulaire (CHC) humain (HepG2, Hep3B, Huh7).

Biochem/physiol Actions

L'acide docosahexaénoïque (DHA) intervient dans la croissance et la physiologie du système nerveux central. Il régule la neurogenèse et la plasticité neuronale chez l'adulte. Le DHA a un rôle important dans le développement du cerveau du fœtus. Il se peut qu'il possède des propriétés antioxydantes et anti-inflammatoires. Le DHA intervient dans la régulation de la fluidité de la membrane cellulaire. Il a un rôle crucial dans plusieurs processus du développement cérébral, notamment la libération des neurotransmetteurs, l'expression génique, la myélinisation, la neuro-inflammation et la différenciation neuronale. Le DHA a des effets anticancéreux sur plusieurs types de cancer.
L'acide docosahexaénoïque (DHA) sert de précurseur pour les molécules de signalisation comme les prostaglandines et les eicosanoïdes.

Packaging

Ampoule scellée.

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Cet article
53171D2410E6627
functional group

carboxylic acid

functional group

carboxylic acid

functional group

ester

functional group

-

biological source

algae

biological source

-

biological source

algae

biological source

synthetic (organic)

assay

≥98%

assay

≥98.0% (GC)

assay

≥97%

assay

≥99% (capillary GC)

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

shipped in

dry ice

shipped in

-

shipped in

ambient

shipped in

dry ice

Quality Level

200

Quality Level

100

Quality Level

100

Quality Level

200


Still not finding the right product?


Classe de stockage

10 - Combustible liquids

wgk

WGK 3

flash_point_f

143.6 °F - closed cup

flash_point_c

62 °C - closed cup

ppe

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



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Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents



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
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
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



Numéro d'article de commerce international

RéférenceGTIN
D2534-1G04061835543861
D2534-100MG04061835543854
D2534-25MG04061835543878

Questions

1–10 of 10 Questions  
  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer
    1. 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/418/501/product-dating-information-06-25-mk.pdf

      Helpful?

  2. Can I use regular tips and vials instead of glass?

    1 answer
    1. 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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  3. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer
    1. 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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  4. 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
    1. 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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  5. 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
    1. D2534 is not a solution; it is a neat oil. The density of D2534 is approximately 0.95 g/mL.

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  6. 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
    1. 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.

      Helpful?

  7. 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
    1. 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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  8. What is the Department of Transportation shipping information for this product?

    1 answer
    1. 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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  9. 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
    1. Yes, this product's double bond configuration is cis.

      Helpful?

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

    1 answer
    1. 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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