4-Hydroxymethyl-3-methoxy-phenoxyacetic acid is an aromatic, non-proteinogenic amino acid derivative featuring a phenoxyacetic acid framework bearing a 3-methoxy substituent and a hydroxymethyl group on the aromatic ring. The molecule contains a carboxylic acid functional group and an ether-linked phenoxy motif that provides a polarizable aromatic side-chain environment, with no amino stereocenter specified in the product name. It is used as a chemically defined building block for preparing modified amino acid and peptide analogues, enabling structure-activity studies, and supporting analytical method development where aromatic functional handles and defined substitution patterns are required.
CAT No: CP27515
CAS No:83590-77-6
Synonyms/Alias:4-Hydroxymethyl-3-methoxyphenoxyacetic acid;83590-77-6;2-[4-(hydroxymethyl)-3-methoxyphenoxy]acetic acid;[4-(hydroxymethyl)-3-methoxyphenoxy]acetic acid;ST50320037;ACMC-20amgk;3-M-4-Hmpaa;AC1Q5WPZ;AC1L34CX;55708_ALDRICH;SCHEMBL150965;55708_FLUKA;CTK5F0886;MolPort-003-936-717;KST-1A8735;ZINC156916;5625AH;AR-1A9051;AKOS024307505;MCULE-1369228566;TRA-0205899;OR015710;DB-056724;KB-239016;TC-168779;4-Hydroxymethyl-3-methoxyphenoxyacetic acid;2-(4-(Hydroxymethyl)-3-methoxyphenoxy)acetic acid;2-[4-(hydroxymethyl)-3-methoxyphenoxy]acetic acid;4-(hydroxymethyl)-3-methoxyphenoxyacetic acid;3-Methoxy-4-hydroxymethylphenoxyacetic acid;3-M-4-Hmpaa;4-hydroxymethyl-3-methoxy-phenoxyacetic acid;SCHEMBL150965;DTXSID20232447;HMPA Linker (4-Hydroxymethyl-3-methoxyphenoxyacetic acid);CHEBI:190017;MFCD00134896;AKOS024307505;BS-42265;DB-056724;F96451;Phenoxyacetic acid, 4-hydroxymethyl-3-methoxy-;Acetic acid, (4-(hydroxymethyl)-3-methoxyphenoxy)-;4-Hydroxymethyl-3-methoxyphenoxyacetic acid, >=97.0%;C52603ED-9557-4488-9935-EC263291662E
4-Hydroxymethyl-3-methoxy-phenoxyacetic acid is an aromatic phenoxyacetic acid derivative bearing a benzylic hydroxymethyl group and a methoxy substituent, providing a combination of acidic functionality and a chemically addressable alcohol for downstream derivatization. This structure is commonly handled as a specialty amino-acid-like building block in medicinal chemistry and specialty chemical synthesis workflows where controlled functional group placement on an aromatic scaffold is required.
1. Phenoxyacetic Intermediate Synthesis
4-Hydroxymethyl-3-methoxy-phenoxyacetic acid is used as a downstream chemical intermediate for constructing substituted phenoxyacetic acid motifs found in bioactive small-molecule scaffolds and related structure-activity relationship (SAR) programs. Researchers in medicinal chemistry and process development value the carboxylic acid handle for straightforward conversion into activated derivatives, while the hydroxymethyl group enables additional functionalization steps to tune polarity, hydrogen-bonding capacity, and steric presentation on the aromatic core.
2. Medicinal Chemistry SAR Building Block
4-Hydroxymethyl-3-methoxy-phenoxyacetic acid supports iterative analog synthesis in small-molecule discovery chemistry, particularly when a phenoxyacetic acid pharmacophore needs substitution at the aromatic ring and at the benzylic alcohol position. Medicinal chemistry groups use this compound to generate libraries of analogs that probe how methoxy substitution and benzylic hydroxymethyl functionality influence physicochemical properties and binding-site interactions, while the defined aromatic substitution pattern helps maintain consistent structure across a series.
3. Polymer And Surface Functionalization
4-Hydroxymethyl-3-methoxy-phenoxyacetic acid is also used in materials chemistry where phenoxyacetic acid derivatives serve as functional monomer precursors or anchoring groups for polymer modification. The presence of both a carboxylic acid and a hydroxymethyl group allows conversion into coupling-ready forms for attaching the aromatic moiety to polymer backbones or surfaces, supporting the creation of tailored materials with controlled aromatic content and hydrogen-bonding functionality for coatings, specialty polymers, or surface-modified substrates.
4. Chiral Derivative Development
4-Hydroxymethyl-3-methoxy-phenoxyacetic acid can be leveraged in chiral intermediate development workflows when stereodefined derivatives are required from a benzylic hydroxymethyl-bearing scaffold. Synthetic chemistry teams use the compound as a starting point to prepare enantiomerically enriched or diastereomerically separated analogs for downstream evaluation in asymmetric synthesis programs, process screening, and stereochemical SAR studies where the benzylic position is a practical locus for stereochemical control.
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