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106615

Sigma-Aldrich

2,2-Bis(hydroxymethyl)propionic acid

98%

Synonym(s):

Bis-MPA, DMPA®, Dimethylolpropionic acid

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About This Item

Linear Formula:
(HOCH2)2C(CH3)COOH
CAS Number:
4767-03-7
Molecular Weight:
134.13
Beilstein:
1756385
EC Number:
225-306-3
MDL number:
MFCD00004199
UNSPSC Code:
12352100
PubChem Substance ID:
24846739
NACRES:
NA.22
Pricing and availability is not currently available.

vapor density

<1 (vs air)

Quality Level

200

Assay

98%

form

solid

mp

189-191 °C (lit.)

solubility

H2O: soluble
acetone: slightly soluble
benzene: insoluble
methanol: soluble

functional group

carboxylic acid
hydroxyl

SMILES string

CC(CO)(CO)C(O)=O

InChI

1S/C5H10O4/c1-5(2-6,3-7)4(8)9/h6-7H,2-3H2,1H3,(H,8,9)

InChI key

PTBDIHRZYDMNKB-UHFFFAOYSA-N

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Application

2,2-Bis(hydroxymethyl)propionic acid based fourth generation tridendron dendrimer having 48 hydroxyl groups was synthesized[1].
2,2-Bis(hydroxymethyl)propionic acid is commonly used as an AB2 monomer for the synthesis of hyperbranched (hb) polymers and dendrimers.[2][3]
2,2-Bis(hydroxymethyl)propionic acid was used in the synthesis and characterization studies of polyurethane dispersion modified with polymethylsiloxane (Si-PUD) and its nanocomposites incorporated with clays[4].2,2-Bis(hydroxymethyl)propionic acid based dendrimers have potent applications as delivery systems for potent anticancer drugs such as cisplatin and doxorubicin, as well as agents for both boron neutron capture therapy and photodynamic therapy[5].
Simple derivatives of this acid have been used to construct dendritic architectures via the "click" azide-acetylene cycloaddition.[6]

Legal Information

DMPA is a registered trademark of GEO Specialty Chemicals, Inc.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H319

Hazard Classifications

Eye Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000364321
0000364321
MKCQ7896
MKCP7788
MKCP5337

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Kazuki Fukushima et al.
Biomaterials science, 7(6), 2288-2296 (2019-04-25)
Cationic aliphatic polycarbonates bearing primary ammonium side chains have been developed with relatively high molecular weights and controlled macromolecular architectures. These polycarbonates exhibit reasonable antimicrobial activity against Gram-negative and Gram-positive bacteria. The prepared homopolymers could be effective against Gram-negative bacteria
First divergent strategy using two AB2 unprotected monomers for the rapid synthesis of dendrimers.
Brauge L, et al.
Journal of the American Chemical Society, 123(27), 6698-6699 (2001)
Structure buildup in hyperbranched polymers from 2, 2-bis (hydroxymethyl) propionic acid.
Magnusson H, et al.
Macromolecules, 33(8), 3099-3104 (2000)
Synthesis and Characterization of Siloxane-Modified Polyurethane Dispersion/Clay Nanocomposites.
Noh HH, et al.
Advanced Materials Research, 415, 1196-1199 (2012)
Elizabeth R Gillies et al.
Drug discovery today, 10(1), 35-43 (2005-01-29)
The unique properties of dendrimers, such as their high degree of branching, multivalency, globular architecture and well-defined molecular weight, make them promising new scaffolds for drug delivery. In the past decade, research has increased on the design and synthesis of
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Questions

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

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

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    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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