Home Other Building Blocks Methoxyacetic acid

Methoxyacetic acid

CAS No.:
625-45-6
Catalog Number:
AG00354W
Molecular Formula:
C3H6O3
Molecular Weight:
90.0779
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
5g
96%
In Stock USA
United States
$25
- +
25g
96%
In Stock USA
United States
$50
- +
100g
96%
In Stock USA
United States
$100
- +
Product Description
Catalog Number:
AG00354W
Chemical Name:
Methoxyacetic acid
CAS Number:
625-45-6
Molecular Formula:
C3H6O3
Molecular Weight:
90.0779
MDL Number:
MFCD00064520
IUPAC Name:
2-methoxyacetic acid
InChI:
InChI=1S/C3H6O3/c1-6-2-3(4)5/h2H2,1H3,(H,4,5)
InChI Key:
RMIODHQZRUFFFF-UHFFFAOYSA-N
SMILES:
COCC(=O)O
EC Number:
210-894-6
UNII:
F11T1H7Q7W
NSC Number:
7300
UN Number:
3265
Properties
Complexity:
50  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
90.032g/mol
Formal Charge:
0
Heavy Atom Count:
6  
Hydrogen Bond Acceptor Count:
3  
Hydrogen Bond Donor Count:
1  
Isotope Atom Count:
0
Molecular Weight:
90.078g/mol
Monoisotopic Mass:
90.032g/mol
Rotatable Bond Count:
2  
Topological Polar Surface Area:
46.5A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
-0.3  
Literature
Title Journal
Mono-(2-ethylhexyl) phthalate-induced Sertoli cell injury stimulates the production of pro-inflammatory cytokines in Fischer 344 rats. Reproductive toxicology (Elmsford, N.Y.) 20170401
Fingerprinting of neurotoxic compounds using a mouse embryonic stem cell dual luminescence reporter assay. Archives of toxicology 20170101
Aminomethylphosphonic acid and methoxyacetic acid induce apoptosis in prostate cancer cells. International journal of molecular sciences 20150501
Assessment of developmental delay in the zebrafish embryo teratogenicity assay. Toxicology in vitro : an international journal published in association with BIBRA 20130201
Endocrine disruptor regulation of microRNA expression in breast carcinoma cells. PloS one 20120101
Hematological effects of exposure to mixtures of selected ethylene glycol alkyl ethers in rats. Pharmacological reports : PR 20120101
Water extract from the leaves of Withania somnifera protect RA differentiated C6 and IMR-32 cells against glutamate-induced excitotoxicity. PloS one 20120101
Chemical class-specific gene expression changes in the zebrafish embryo after exposure to glycol ether alkoxy acids and 1,2,4-triazole antifungals. Reproductive toxicology (Elmsford, N.Y.) 20110901
Relative embryotoxicity of two classes of chemicals in a modified zebrafish embryotoxicity test and comparison with their in vivo potencies. Toxicology in vitro : an international journal published in association with BIBRA 20110401
Free Rhodium (II) citrate and rhodium (II) citrate magnetic carriers as potential strategies for breast cancer therapy. Journal of nanobiotechnology 20110101
Complex modulation of androgen responsive gene expression by methoxyacetic acid. Reproductive biology and endocrinology : RB&E 20110101
Ashwagandha leaf derived withanone protects normal human cells against the toxicity of methoxyacetic acid, a major industrial metabolite. PloS one 20110101
Physiologically based pharmacokinetic modeling: methodology, applications, and limitations with a focus on its role in pediatric drug development. Journal of biomedicine & biotechnology 20110101
Wired on steroids: sexual differentiation of the brain and its role in the expression of sexual partner preferences. Frontiers in endocrinology 20110101
Ethylene glycol monomethyl ether-induced toxicity is mediated through the inhibition of flavoprotein dehydrogenase enzyme family. Toxicological sciences : an official journal of the Society of Toxicology 20101201
A predictive ligand-based Bayesian model for human drug-induced liver injury. Drug metabolism and disposition: the biological fate of chemicals 20101201
Embryotoxicant-specific transcriptomic responses in rat postimplantation whole-embryo culture. Toxicological sciences : an official journal of the Society of Toxicology 20101201
Toxicant-induced leakage of germ cell-specific proteins from seminiferous tubules in the rat: relationship to blood-testis barrier integrity and prospects for biomonitoring. Toxicological sciences : an official journal of the Society of Toxicology 20101001
In vitro-Ishikawa cell test for assessing tissue-specific chemical effects on human endometrium. Reproductive toxicology (Elmsford, N.Y.) 20100801
Monitoring developmental toxicity in the embryonic stem cell test using differential gene expression of differentiation-related genes. Toxicological sciences : an official journal of the Society of Toxicology 20100701
Decrease of intracellular pH as possible mechanism of embryotoxicity of glycol ether alkoxyacetic acid metabolites. Toxicology and applied pharmacology 20100601
Assignment of the structure of petrocortyne A by mixture syntheses of four candidate stereoisomers. The Journal of organic chemistry 20100507
Impact of methoxyacetic acid on mouse Leydig cell gene expression. Reproductive biology and endocrinology : RB&E 20100101
Effect of high intratesticular estrogen on global gene expression and testicular cell number in rats. Reproductive biology and endocrinology : RB&E 20100101
Physiological effects and mechanisms of action of endocrine disrupting chemicals that alter estrogen signaling. Hormones (Athens, Greece) 20100101
Fatty acids derived from royal jelly are modulators of estrogen receptor functions. PloS one 20100101
The short-chain fatty acid methoxyacetic acid disrupts endogenous estrogen receptor-alpha-mediated signaling. Environmental health perspectives 20091101
Differential expression of N-Myc downstream regulated gene 2 (NDRG2) in the rat testis during postnatal development. Cell and tissue research 20090801
Interactions of methoxyacetic acid with androgen receptor. Toxicology and applied pharmacology 20090715
Relative developmental toxicity of glycol ether alkoxy acid metabolites in the embryonic stem cell test as compared with the in vivo potency of their parent compounds. Toxicological sciences : an official journal of the Society of Toxicology 20090701
Enhanced ERbeta immunoexpression and apoptosis in the germ cells of cimetidine-treated rats. Reproductive biology and endocrinology : RB&E 20090101
Evaluation of the embryotoxic potency of compounds in a newly revised high throughput embryonic stem cell test. Toxicological sciences : an official journal of the Society of Toxicology 20081001
Esterification in ionic liquids: the influence of solvent basicity. The Journal of organic chemistry 20080718
Lewis base activation of Lewis acids: catalytic, enantioselective addition of glycolate-derived silyl ketene acetals to aldehydes. The Journal of organic chemistry 20080620
Methoxyacetic acid-induced spermatocyte death is associated with histone hyperacetylation in rats. Biology of reproduction 20080501
Chiral resolutions of (9-anthryl)methoxyacetic acid and (9-anthryl)hydroxyacetic acid by capillary electrophoresis. Chirality 20080101
Correlation between urinary methoxyacetic acid and exposure of ethylene glycol dimethyl ether in a lithium battery plant. International archives of occupational and environmental health 20071001
Correlation of appearance of metastasis-associated protein1 (Mta1) with spermatogenesis in developing mouse testis. Cell and tissue research 20070801
Synthesis of C13-C25 fragment of 24-demethylbafilomycin C(1) via diastereoselective aldol reactions of a ketone boron enolate as the key step. The Journal of organic chemistry 20070622
A new synthesis of lysophosphatidylcholines and related derivatives. Use of p-toluenesulfonate for hydroxyl group protection. The Journal of organic chemistry 20070302
Quantification of PERF 15 mRNA in tissue sections from rat testes. Acta histochemica et cytochemica 20061228
Diethylene glycol monomethyl ether, ethylene glycol monomethyl ether and the metabolite, 2-methoxyacetic acid affect in vitro chondrogenesis. Reproductive toxicology (Elmsford, N.Y.) 20061101
Molecular basis for the enhanced lipase-catalyzed N-acylation of 1-phenylethanamine with methoxyacetate. Chembiochem : a European journal of chemical biology 20061101
Prediction of in vivo embryotoxic effect levels with a combination of in vitro studies and PBPK modelling. Toxicology letters 20060801
Endocrine-disrupting chemicals use distinct mechanisms of action to modulate endocrine system function. Endocrinology 20060601
Gas chromatography analysis of urinary alkoxyacetic acids as biomarkers of exposure to aliphatic alkyl ethers. Journal of analytical toxicology 20060501
A new multiphasic buffer system for benzyldimethyl-n-hexadecylammonium chloride polyacrylamide gel electrophoresis of proteins providing efficient stacking. Electrophoresis 20060201
Testicular toxicity of candidate fuel additive 1,6-dimethoxyhexane: comparison with several similar aliphatic ethers. Toxicological sciences : an official journal of the Society of Toxicology 20060101
The alkoxyacetic acids as calcium and magnesium chelating agents in vitro. Acta poloniae pharmaceutica 20060101
Short-term oral toxicity of butyl ether, ethyl hexyl ether, methyl heptyl ether and 1,6-dimethoxyhexane in male rats and the role of 2-methoxyacetic acid. Toxicology 20051015
Urinary methoxyacetic acid as an indicator of occupational exposure to ethylene glycol dimethyl ether. International archives of occupational and environmental health 20050901
A teratoproteomics analysis: heat shock protein 70 is upregulated in mouse forelimb bud by methoxyacetic acid treatment. Birth defects research. Part A, Clinical and molecular teratology 20050701
Quantification of stem cell factor mRNA levels in the rat testis: usefulness of clusterin mRNA as a marker of the amount of mRNA of Sertoli cell origin in post pubertal rats. The Journal of endocrinology 20050701
Biotic and abiotic degradation behaviour of ethylene glycol monomethyl ether (EGME). Water research 20050501
The mechanism of ethylene glycol ether reproductive and developmental toxicity and evidence for adverse effects in humans. Toxicology letters 20050328
Modulation of MAA-induced apoptosis in male germ cells: role of Sertoli cell P/Q-type calcium channels. Reproductive biology and endocrinology : RB&E 20050101
Discriminative power of an assay for automated in vitro screening of teratogens. Toxicology in vitro : an international journal published in association with BIBRA 20040801
Evaluation of the protective effectiveness of gloves from occupational exposure to 2-methoxyethanol using the biomarkers of 2-methoxyacetic acid levels in the urine and plasma. Occupational and environmental medicine 20040801
Hepatic effects in workers exposed to 2-methoxy ethanol. Journal of occupational and environmental medicine 20040701
Determination of urinary metabolites of alkyl cellosolves by solid phase extraction and GC/FID. Journal of occupational health 20040701
Short-chain fatty acids enhance nuclear receptor activity through mitogen-activated protein kinase activation and histone deacetylase inhibition. Proceedings of the National Academy of Sciences of the United States of America 20040504
Sertoli cell modulates MAA-induced apoptosis of germ cells throughout voltage-operated calcium channels. FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20040201
Increased expression of estrogen receptor beta in pachytene spermatocytes after short-term methoxyacetic acid administration. Journal of andrology 20040101
AACR Special Conference: Advances in Breast Cancer Research--Genetics, Biology, and Clinical Implications, Huntington Beach, California, USA, 8-12 October 2003. Breast cancer research : BCR 20040101
The laminin binding protein p40 is involved in inducing limb abnormality of mouse fetuses as the effects of methoxyacetic acid treatment. Toxicological sciences : an official journal of the Society of Toxicology 20030901
Methoxyacetic acid disregulation of androgen receptor and androgen-binding protein expression in adult rat testis. Biology of reproduction 20030401
Follow up study of haematological effects in workers exposed to 2-methoxyethanol. Occupational and environmental medicine 20030201
Significance of 2-methoxypropionic acid formed from beta-propylene glycol monomethyl ether: integration of pharmacokinetic and developmental toxicity assessments in rabbits. Toxicological sciences : an official journal of the Society of Toxicology 20030201
Dynamics of testicular germ cell apoptosis in normal mice and transgenic mice overexpressing rat androgen-binding protein. Reproductive biology and endocrinology : RB&E 20030101
Involvement of caspase 3 mediated apoptosis in hematopoietic cytotoxicity of metabolites of ethylene glycol monomethyl ether. Industrial health 20021001
N-acetylcysteine prevents MAA induced male germ cell apoptosis: role of glutathione and cytochrome c. FEBS letters 20020911
Heat shock-initiated apoptosis is accelerated and removal of damaged cells is delayed in the testis of clusterin/ApoJ knock-out mice. Biology of reproduction 20020401
Selection of test chemicals for the ECVAM international validation study on in vitro embryotoxicity tests. European Centre for the Validation of Alternative Methods. Alternatives to laboratory animals : ATLA 20020101
Effects of acute and chronic doses of methoxy acetic acid on hamster sperm fertilising ability. Asian journal of andrology 20010901
2-Methoxyethanol metabolism, embryonic distribution, and macromolecular adduct formation in the rat: the effect of radiofrequency radiation-induced hyperthermia. Toxicology letters 20010531
Differential expression and regulation of the retinoblastoma family of proteins during testicular development and spermatogenesis: roles in the control of germ cell proliferation, differentiation and apoptosis. Oncogene 20010315
Urinary 2-methoxy acetic acid accumulation in response to 2-methoxy ethanol exposure. Archives of environmental health 20010101
Protein kinase activity is central to rat germ cell apoptosis induced by methoxyacetic acid. Toxicologic pathology 20010101
Expression of testicular fatty acid-binding protein PERF 15 during germ cell apoptosis. Development, growth & differentiation 20000801
Bcl-w forms complexes with Bax and Bak, and elevated ratios of Bax/Bcl-w and Bak/Bcl-w correspond to spermatogonial and spermatocyte apoptosis in the testis. Molecular endocrinology (Baltimore, Md.) 20000501
Rat pachytene spermatocytes down-regulate a polo-like kinase and up-regulate a thiol-specific antioxidant protein, whereas sertoli cells down-regulate a phosphodiesterase and up-regulate an oxidative stress protein after exposure to methoxyethanol and methoxyacetic acid. Endocrinology 19980801
Accumulation of clusterin/sulfated glycoprotein-2 in degenerating pachytene spermatocytes of adult rats treated with methoxyacetic acid. Biology of reproduction 19971001
Fetal hematopoietic alterations after maternal exposure to ethylene glycol monomethyl ether: prolymphoid cell targeting. Toxicology and applied pharmacology 19941101
Stage-dependent expression of mRNA for cyclic protein 2 during spermatogenesis is modulated by elongate spermatids. Molecular and cellular endocrinology 19930701
Pathogenesis of limb malformations in mice induced by methoxyacetic acid. Hiroshima journal of medical sciences 19910901
Pattern of limb malformations in mice induced by methoxyacetic acid. Hiroshima journal of medical sciences 19910901
Evidence that secretion of immunoactive inhibin by seminiferous tubules from the adult rat testis is regulated by specific germ cell types: correlation between in vivo and in vitro studies. Endocrinology 19910101
Ventral duplication of the autopod: chemical induction by methoxyacetic acid in rat embryos. Development (Cambridge, England) 19870101
Studies on the toxicity of some glycol ethers and alkoxyacetic acids in primary testicular cell cultures. Toxicology and applied pharmacology 19850701
Testicular toxicity produced by ethylene glycol monomethyl and monoethyl ethers in the rat. Environmental health perspectives 19840801
Properties