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D6182

Sigma-Aldrich

DOTAP chloride

≥98% (TLC), powder

Synonym(s):

N-[1-(2,3-Dioleoyloxy)propyl]-N,N,N-trimethylammonium chloride

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About This Item

Empirical Formula (Hill Notation):
C42H80ClNO4
CAS Number:
132172-61-3
Molecular Weight:
698.54
MDL number:
MFCD01310872
UNSPSC Code:
12352211
PubChem Substance ID:
329798823
NACRES:
NA.32
Pricing and availability is not currently available.

Quality Level

200

Assay

≥98% (TLC)

form

powder

shipped in

dry ice

storage temp.

−20°C

SMILES string

[H]C(C[N+](C)(C)C)(OC(CCCCCCC/C=C\CCCCCCCC)=O)COC(CCCCCCC/C=C\CCCCCCCC)=O.[Cl-]

InChI

1S/C42H80NO4.ClH/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-34-36-41(44)46-39-40(38-43(3,4)5)47-42(45)37-35-33-31-29-27-25-23-21-19-17-15-13-11-9-7-2;/h20-23,40H,6-19,24-39H2,1-5H3;1H/q+1;/p-1/b22-20-,23-21-;

InChI key

KSXTUUUQYQYKCR-LQDDAWAPSA-M

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Application

1,2-dioleoyloxy-3-(trimethylammonium)propane (DOTAP) chloride has been used for the preparation of cationic liposome and liposome-DNA complex.[1] It has also been used to assess tumor necrosis factor α (TNF- α) production.[2]
Cationic liposome-forming compound for transfection of DNA, RNA and other negatively charged molecules into eukaryotic cells. Mixing DOTAP with DNA results in spontaneously formed stable complexes that can be directly added to cell culture medium. These complexes fuse with the cell membrane and release DNA into the cytoplasm. The cells are transfected efficiently without cytotoxic effects. Use approximately 5-10 μg DOTAP per μg DNA and approximately 10-20 μg DOTAP per mL cell culture medium. The optimal working concentration and transfection time depends in part on the cell line used, and the type of material (RNA, DNA, protein) loaded.

Biochem/physiol Actions

1,2-dioleoyloxy-3-(trimethylammonium)propane (DOTAP) chloride is useful in liposome preparation, without the use of helper lipid. DOTAP chloride is soluble in dimethyl sulfoxide (DMSO) and ethanol, this defines its function as a transfection agent.[3]

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
SLCM5565
SLCG1712
SLCC2373
SLBZ9601
SLBG7267V

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A novel strategy for tumour therapy combining cell apoptosis and active immunity induced by caspy2, a zebrafish caspase
Liu L, et al.
Journal of Cellular and Molecular Medicine, 13(8b), 2271-2281 (2009)
A simplified direct lipid mixing lipoplex preparation: Comparison of liposomal-, dimethylsulfoxide-, and ethanol-based methods
Meisel JW and Gokel GW
Scientific Reports, 6, 27662-27662 (2016)
Ju-mei Zhao et al.
FASEB journal : official publication of the Federation of American Societies for Experimental Biology, 22(12), 4272-4280 (2008-08-22)
The matrix (M) protein of vesicular stomatitis virus (VSV) plays a key role in inducing cell apoptosis during infection. To investigate whether M protein-mediated apoptosis could be used in cancer therapy, its cDNA was amplified and cloned into eukaryotic expression
Structurally distinct phosphatases CD45 and CD148 both regulate B cell and macrophage immunoreceptor signaling
Zhu JW, et al.
Immunity, 28(2), 183-196 (2008)

Questions

1–2 of 2 Questions  

  1. 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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  2. 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/449/386/product-dating-information-mk.pdf

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