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129585

Sigma-Aldrich

Maleimide

99%

Synonym(s):

2,5-Pyrroledione

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About This Item

Empirical Formula (Hill Notation):
C4H3NO2
CAS Number:
541-59-3
Molecular Weight:
97.07
Beilstein:
106910
EC Number:
208-787-4
MDL number:
MFCD00005494
UNSPSC Code:
12352100
PubChem Substance ID:
24847914
NACRES:
NA.22
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Quality Level

200

Assay

99%

form

powder

mp

91-93 °C (lit.)

functional group

maleimide

SMILES string

O=C1NC(=O)C=C1

InChI

1S/C4H3NO2/c6-3-1-2-4(7)5-3/h1-2H,(H,5,6,7)

InChI key

PEEHTFAAVSWFBL-UHFFFAOYSA-N

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General description

Maleimide (2,5-Pyrroledione) is a new nanoparticle surface functional group which favors easy conjugation with cell penetration peptides. The conjugation is enabled via click chemistry to preserve its biofunctions[1].

Maleimide is used as a dienophile in Diels Alder reaction for the synthesis of macromolecules.[2]

Application

Rhodium-catalyzed conjugate arylation with arylboronic acids.[3]
The maleimide-functionalized silica beads were used to immobilize the bovine serum albumin (BSA)-boronic acid (BA) conjugates[4].

Pictograms

Skull and crossbonesCorrosion
GHS06,GHS05

Signal Word

Danger

Hazard Statements

H300,H314,H317

Hazard Classifications

Acute Tox. 2 Oral - Eye Dam. 1 - Skin Corr. 1B - Skin Sens. 1

Storage Class Code

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

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
STBL4412
SDBB0918
STBL1348
STBL3213
STBK7648

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Guangxue Feng et al.
Small (Weinheim an der Bergstrasse, Germany), 10(6), 1212-1219 (2013-12-18)
Single-chain conjugated polymer (CP) dots embedded nanoparticles (NPs) bearing cell penetration peptide (TAT) as surface ligands are synthesized for long term cancer cell tracing applications. The CPNPs are fabricated by matrix-encapsulation method and the embedded CPs can be modulated into
Paulo L Onuchic et al.
Scientific reports, 9(1), 12161-12161 (2019-08-23)
Liquid-liquid phase separation (LLPS) of RNA-protein complexes plays a major role in the cellular function of membraneless organelles (MLOs). MLOs are sensitive to changes in cellular conditions, such as fluctuations in cytoplasmic ion concentrations. To investigate the effect of these
Satya Nandana Narla et al.
Biochemical and biophysical research communications, 443(2), 562-567 (2013-12-12)
We report bovine serum albumin (BSA)-boronic acid (BA) conjugates as lectin mimetics and their glyco-capturing capacity. The BSA-BA conjugates were synthesized by amidation of carboxylic acid groups in BSA with aminophenyl boronic acid in the presence of EDC, and were
Meng Ke et al.
PLoS computational biology, 13(6), e1005603-e1005603 (2017-06-16)
GLUT1 facilitates the down-gradient translocation of D-glucose across cell membrane in mammals. XylE, an Escherichia coli homolog of GLUT1, utilizes proton gradient as an energy source to drive uphill D-xylose transport. Previous studies of XylE and GLUT1 suggest that the
The furan/maleimide Diels--Alder reaction: A versatile click--unclick tool in macromolecular synthesis
Gandini A.
Progress in Polymer Science, 38, 1-29 (2013)
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Questions

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  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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