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166952

Sigma-Aldrich

2-Hydroxybenzyl alcohol

99%

Synonym(s):

Salicyl alcohol, Saligenin

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About This Item

Linear Formula:
HOC6H4CH2OH
CAS Number:
90-01-7
Molecular Weight:
124.14
Beilstein:
1907195
EC Number:
201-960-5
MDL number:
MFCD00004617
UNSPSC Code:
12352100
PubChem Substance ID:
24850189
NACRES:
NA.22

Assay

99%

form

solid

mp

83-85 °C (lit.)

solubility

ethanol: soluble 5%, clear to very slightly hazy, colorless to light yellow

SMILES string

OCc1ccccc1O

InChI

1S/C7H8O2/c8-5-6-3-1-2-4-7(6)9/h1-4,8-9H,5H2

InChI key

CQRYARSYNCAZFO-UHFFFAOYSA-N

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General description

2-Hydroxybenzyl alcohol participates in the selective ring opening reaction of 4H-1,3,2-benzodioxasilines.

2-Hydroxybenzyl alcohol can be used as a coupling reagent to synthesize O-heterocycles.

Application

2-Hydroxybenzyl alcohol was used in gastrodin production via biotransformation by cultured cells of Aspergillus foetidus and Penicillium cyclopium.

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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Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Linlin Fan et al.
Applied biochemistry and biotechnology, 170(1), 138-148 (2013-03-14)
The objective of this work was to take advantage of the resting cells of suitable fungus as an in vitro model to prepare gastrodin from p-2-hydroxybenzyl alcohol (HBA), which mainly exists in the metabolites of the plant Gastrodia elata Blume.
Seung-Heon Yoon et al.
Carbohydrate research, 339(8), 1517-1529 (2004-06-05)
Beta-Salicin is a naturally occurring glycoside found in the bark of poplar and willow trees. Ancient man used it as an analgesic and antipyretic. It has a D-glucopyranose unit attached by a beta-linkage to the phenolic hydroxyl of salicyl alcohol.
M Brückmann et al.
Insect biochemistry and molecular biology, 32(11), 1517-1523 (2003-01-18)
Larvae of a number of chrysomelid leaf beetles sequester phenol glucosides such as salicin from their food plants, i.e. Salix and Populus spp. Salicin is hydrolyzed in the glandular reservoir of the defensive glands. The resulting salicyl alcohol (saligenin) is
Teruaki Akao et al.
Planta medica, 68(8), 714-718 (2002-09-11)
Pharmacokinetic and pharmacological studies were performed to compare the antipyretic effects of salicin (SL), saligenin (SG, an aglycone of SL) and salicylic acid (SA, an active metabolite of SL) in rats. When SL was administered orally to rats, SA appeared
Nicolas Gisch et al.
Journal of medicinal chemistry, 51(21), 6752-6760 (2008-10-07)
Recently we reported on conceptually new enzymatically activated cycloSal-pronucleotides. Now, we developed this concept further with new compounds of this type. The basic idea is fast intracellular cleavage of a functionalized group at the cycloSal residue that results in a
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