625-45-6 | Methoxyacetic acid

Packsize	Purity	Availability	Price	Discounted Price
25g	96%	in stock	$21.00	$15.00
100g	96%	in stock	$55.00	$38.00
500g	96%	in stock	$114.00	$80.00

Description

• Catalog Number: AB46424
• Chemical Name: Methoxyacetic acid
• CAS Number: 625-45-6
• Molecular Formula: C3H6O3
• Molecular Weight: 90.07794
• MDL Number: MFCD00064520
• SMILES: COCC(=O)O
• NSC Number: 7300

Computed Properties

• Complexity: 50
• Covalently-Bonded Unit Count: 1
• Heavy Atom Count: 6
• Hydrogen Bond Acceptor Count: 3
• Hydrogen Bond Donor Count: 1
• Rotatable Bond Count: 2
• XLogP3: -0.3

Upstream Synthesis Route

2-Methoxyacetic acid, also known as O-methylglycolic acid, plays a crucial role in chemical synthesis as a versatile building block for various reactions and processes. This compound is commonly used as a key intermediate in the synthesis of pharmaceuticals, agrochemicals, and specialty chemicals. The presence of the methoxy group (-OCH3) imparts unique reactivity to the molecule, allowing for selective functionalization and formation of complex organic structures. In particular, 2-Methoxyacetic acid is utilized in the preparation of esters, ethers, and amides, serving as a precursor for the modification of functional groups in organic molecules. Its compatibility with a wide range of reagents and reaction conditions makes it a popular choice for organic chemists seeking to introduce specific moieties or motifs into their target compounds. Additionally, 2-Methoxyacetic acid can act as a protecting group for certain reactive functionalities, enabling chemists to carry out multi-step syntheses with enhanced control over regioselectivity and yield. The widespread application of 2-Methoxyacetic acid in chemical synthesis underscores its importance as a valuable tool in the construction of complex molecular architectures for various industrial and academic purposes.

Literature

• 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