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C13408

Sigma-Aldrich

O-(Carboxymethyl)hydroxylamine hemihydrochloride

98%

Synonym(s):

Carboxymethoxylamine hemihydrochloride, (Aminooxy)acetic acid hemihydrochloride, (Carboxymethoxy)amine hemihydrochloride, Hydroxylamine-O-acetic acid hemihydrochloride

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About This Item

Linear Formula:
NH2OCH2COOH · 0.5HCl
CAS Number:
2921-14-4
Molecular Weight:
109.30
Beilstein:
3680528
EC Number:
220-862-3
MDL number:
MFCD00012955
UNSPSC Code:
12352100
PubChem Substance ID:
24892403
NACRES:
NA.22

biological source

synthetic (organic)

Assay

98%

form

crystalline powder
powder or crystals

mp

156 °C (dec.) (lit.)

solubility

water: 100 mg/mL, clear to slightly hazy, colorless to faintly yellow

storage temp.

2-8°C

SMILES string

Cl.NOCC(O)=O.NOCC(O)=O

InChI

1S/2C2H5NO3.ClH/c2*3-6-1-2(4)5;/h2*1,3H2,(H,4,5);1H

InChI key

KBXIJIPYZKPDRU-UHFFFAOYSA-N

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Application

O-(Carboxymethyl)hydroxylamine hemihydrochloride can be used as a reactant to synthesize oximes via condensation with aldehydes and ketones. It can also be used as a potent inhibitor of (pyridoxal 5’-phosphate) PLP-dependent β-lyases.

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
MKCP7588
MKCP4441
MKCL9254
MKCL3876
MKCL0940

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A Sala et al.
Farmaco (Societa chimica italiana : 1989), 46(7-8), 887-897 (1991-07-01)
The synthesis of new 2-(3-bromo-5-isoxazolylideneamino-oxy)acetic acids and their condensation derivatives with suitable beta-lactam nuclei is reported. Their antibacterial properties have been tested in vitro. An interesting activity against Gram-positive bacteria including beta-lactamase-producing microorganisms was found among the cephalosporanic acid derivatives.
Tetrahedron Letters, 34, 4347-4347 (1993)
Characterization of a 5'-aldehyde terminus resulting from the oxidative attack at C5 `of a 2-deoxyribose on DNA
Angeloff A, et al.
Chemical Research in Toxicology, 14, 1413-1420 (2001)
Ches'Nique M Phillips et al.
Cancer research, 77(21), 5741-5754 (2017-09-20)
The trans-sulfuration enzyme cystathionine-β-synthase (CBS) and its product hydrogen sulfide (H2S) are aberrantly upregulated in colorectal cancers, where they contribute to tumor growth and progression by both autocrine and paracrine mechanisms. However, it is unknown whether the CBS/H2S axis plays
Kerry L McPhail et al.
Journal of natural products, 73(11), 1853-1857 (2010-10-29)
A new oxyvinylglycine has been identified as a naturally occurring herbicide that irreversibly arrests germination of the seeds of grassy weeds, such as annual bluegrass (Poa annua), without significantly affecting the growth of established grass seedlings and mature plants or
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