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55730

Sigma-Aldrich

4-(Hydroxymethyl)phenoxyacetic acid

≥97.0%

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About This Item

Empirical Formula (Hill Notation):
C9H10O4
CAS Number:
68858-21-9
Molecular Weight:
182.17
Beilstein/REAXYS Number:
5260336
MDL number:
MFCD00057827
UNSPSC Code:
12352106
PubChem Substance ID:
57651551
NACRES:
NA.22

assay

≥97.0%

reaction suitability

reagent type: cross-linking reagent

mp

112-114 °C

functional group

carboxylic acid
hydroxyl

storage temp.

−20°C

SMILES string

OCC1=CC=C(OCC(O)=O)C=C1

InChI

1S/C9H10O4/c10-5-7-1-3-8(4-2-7)13-6-9(11)12/h1-4,10H,5-6H2,(H,11,12)

InChI key

VUCNQOPCYRJCGQ-UHFFFAOYSA-N

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Other Notes

Linkage agent used in solid-phase peptide synthesis according to the "FMOC-polyamide" technique[1][2][3]

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
1230800
365911/1
401502/1
360842/1
354855/1

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E. Atherton et al.
Journal of the Chemical Society. Chemical Communications, 537-537 (1978)
C T Bui et al.
Journal of peptide science : an official publication of the European Peptide Society, 6(10), 534-538 (2000-11-09)
A replacement of the acetic acid moiety by valeric acid within the 4-hydroxymethylphenoxyacetic acid (HMP) linker (Sheppard RC, Williams BJ. Acid-labile resin linkage agents for use in solid phase peptide synthesis. Int. J. Peptide Protein Res. 1982; 20: 451-454) significantly
A. Dryland et al.
Journal of the Chemical Society. Perkin Transactions 1, 125-125 (1986)
Journal of the Chemical Society. Chemical Communications, 539-539 (1978)
R C Sheppard et al.
International journal of peptide and protein research, 20(5), 451-454 (1982-11-01)
Details are given of the preparation of two acid-labile peptide-resin linkage agents for use in solid phase peptide synthesis, viz. 4-hydroxymethylphenoxy-acetic acid and 3-methoxy-4-hydroxymethylphenoxyacetic acid. The latter is suitable for the preparation of peptide fragments bearing t-butyl-based side chain protecting

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