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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
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Assay

99%

form

solid

mp

83-85 °C (lit.)

solubility

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

functional group

hydroxyl

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[1].

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

Application

2-Hydroxybenzyl alcohol was used in gastrodin production via biotransformation by cultured cells of Aspergillus foetidus and Penicillium cyclopium[3].

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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Certificates of Analysis (COA)

Lot/Batch Number
BCCK3195
BCCL1078
BCCJ7827
BCCH3861
BCCF7040

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Catalytic acceptorless dehydrogenation of amino alcohols and 2-hydroxybenzyl alcohols for annulation reaction under neutral conditions
Pandey AM, et al.
The Journal of Organic Chemistry, 86, 8805-8828 (2021)
Selective ring opening of 4H-1, 3, 2-benzodioxasiline twin monomers.
Kempe P, et al.
New. J. Chem., 35(12), 2735-2739 (2011)
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.
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
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
View All Related Papers

Questions

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  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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