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Wikipedia

Salicyl alcohol

Salicyl alcohol (saligenin) is an organic compound with the formula C6HOH(CH2OH. It is a white solid that is used as a precursor in organic synthesis.[3]

Salicyl alcohol
Names
Preferred IUPAC name
2-(Hydroxymethyl)phenol
Other names
2-Hydroxybenzyl alcohol, Salicain, Diathesin, Saligenin, Saligenol, Salicyl alcohol, α,2-Toluenediol, o-Methylolphenol, 2-Methylolphenol, Salicylic alcohol[1]
Identifiers
  • 90-01-7 Y
3D model (JSmol)
  • Interactive image
ChemSpider
  • 4962
ECHA InfoCard 100.001.782
EC Number
  • 201-960-5
  • 5146
UNII
  • FA1N0842KB Y
  • DTXSID9045843
  • InChI=1S/C7H8O2/c8-5-6-3-1-2-4-7(6)9/h1-4,8-9H,5H2
    Key: CQRYARSYNCAZFO-UHFFFAOYSA-N
  • c1ccc(c(c1)CO)O
Properties
C7H8O2
Molar mass 124.139 g·mol−1
Density 1.16 g/cm3
Melting point 86 °C (187 °F; 359 K)
Boiling point 267 °C (513 °F; 540 K)
67g/L at 22 °C[2]
-76.9·10−6 cm3/mol
Hazards
GHS labelling:
Warning
H315, H319, H335
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
Flash point 134 °C[2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Synthesis and applications edit

Salicyl alcohol is produced by the hydroxymethylation of phenol using formaldehyde:[4]

C6H5OH + CH2O → C6H4OH(CH2OH

Air oxidation of salicyl alcohol gives salicylaldehyde.

C6H4OH(CH2OH + O → C6H4OH(CHO) +H2O

Chemical sweeteners are formed by acetal formation with e.g. isovanillin (Cmp4).[5]

Salicyl alcohol appears as a pharmacophore in several notable β2-adrenoceptor agonists (e.g. salbutamol), as well as in synthetic estrone analogs, e.g. CID:22940780 or CID:154236944.

Biosynthesis edit

Salicyl alcohol is the precursor of salicylic acid.[6] It is formed from salicin by enzymatic hydrolysis by Salicyl-alcohol beta-D-glucosyltransferase or by acid hydrolysis.

See also edit

References edit

  1. ^ "2-Hydroxybenzyl alcohol". chemicalbook.com.
  2. ^ a b "salicylic alcohol". chemspider.com.
  3. ^ Vishwakarma Singh, Mini Porinchu, Punitha Vedantham, Pramod K. Sahu1 (2005). "Synthesis of 9-Spiroepoxy-endo-Tricyclo[5.2.2.0]undeca-4,10-dien-8-one". Organic Syntheses. 81: 171. doi:10.15227/orgsyn.081.0171.{{cite journal}}: CS1 maint: multiple names: authors list (link) CS1 maint: numeric names: authors list (link)
  4. ^ Maliverney, Christian; Mulhauser, Michel (2000). "Hydroxybenzaldehydes". Kirk-Othmer Encyclopedia of Chemical Technology. doi:10.1002/0471238961.0825041813011209.a01. ISBN 978-0-471-48494-3.
  5. ^ Bassoli, Angela; Merlini, Lucio; Morini, Gabriella (2002). "Isovanillyl sweeteners. From molecules to receptors". Pure and Applied Chemistry. 74 (7): 1181–1187. doi:10.1351/pac200274071181. ISSN 1365-3075. S2CID 53554546.
  6. ^ Seo, Eun-Seong; Lee, Jin-Ha; Park, Ji-Young; Kim, Doman; Han, Ho-Jae; Robyt, John F. (2005). "Enzymatic synthesis and anti-coagulant effect of salicin analogs by using the Leuconostoc mesenteroides glucansucrase acceptor reaction". Journal of Biotechnology. 117 (1): 31–38. doi:10.1016/j.jbiotec.2004.10.013. PMID 15831245.

salicyl, alcohol, saligenin, organic, compound, with, formula, c6hoh, ch2oh, white, solid, that, used, precursor, organic, synthesis, names, preferred, iupac, name, hydroxymethyl, phenol, other, names, hydroxybenzyl, alcohol, salicain, diathesin, saligenin, sa. Salicyl alcohol saligenin is an organic compound with the formula C6HOH CH2OH It is a white solid that is used as a precursor in organic synthesis 3 Salicyl alcohol Names Preferred IUPAC name 2 Hydroxymethyl phenol Other names 2 Hydroxybenzyl alcohol Salicain Diathesin Saligenin Saligenol Salicyl alcohol a 2 Toluenediol o Methylolphenol 2 Methylolphenol Salicylic alcohol 1 Identifiers CAS Number 90 01 7 Y 3D model JSmol Interactive image ChemSpider 4962 ECHA InfoCard 100 001 782 EC Number 201 960 5 PubChem CID 5146 UNII FA1N0842KB Y CompTox Dashboard EPA DTXSID9045843 InChI InChI 1S C7H8O2 c8 5 6 3 1 2 4 7 6 9 h1 4 8 9H 5H2Key CQRYARSYNCAZFO UHFFFAOYSA N SMILES c1ccc c c1 CO O Properties Chemical formula C 7H 8O 2 Molar mass 124 139 g mol 1 Density 1 16 g cm3 Melting point 86 C 187 F 359 K Boiling point 267 C 513 F 540 K Solubility in water 67g L at 22 C 2 Magnetic susceptibility x 76 9 10 6 cm3 mol Hazards GHS labelling Pictograms Signal word Warning Hazard statements H315 H319 H335 Precautionary statements P261 P264 P271 P280 P302 P352 P304 P340 P305 P351 P338 P312 P321 P332 P313 P337 P313 P362 P403 P233 P405 P501 Flash point 134 C 2 Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Infobox references Contents 1 Synthesis and applications 2 Biosynthesis 3 See also 4 ReferencesSynthesis and applications editSalicyl alcohol is produced by the hydroxymethylation of phenol using formaldehyde 4 C6H5OH CH2O C6H4OH CH2OH Air oxidation of salicyl alcohol gives salicylaldehyde C6H4OH CH2OH O C6H4OH CHO H2O Chemical sweeteners are formed by acetal formation with e g isovanillin Cmp4 5 Salicyl alcohol appears as a pharmacophore in several notable b2 adrenoceptor agonists e g salbutamol as well as in synthetic estrone analogs e g CID 22940780 or CID 154236944 Biosynthesis editSalicyl alcohol is the precursor of salicylic acid 6 It is formed from salicin by enzymatic hydrolysis by Salicyl alcohol beta D glucosyltransferase or by acid hydrolysis See also editGastrodigenin 4 hydroxybenzyl alcohol Discovery and development of beta2 agonistsReferences edit 2 Hydroxybenzyl alcohol chemicalbook com a b salicylic alcohol chemspider com Vishwakarma Singh Mini Porinchu Punitha Vedantham Pramod K Sahu1 2005 Synthesis of 9 Spiroepoxy endo Tricyclo 5 2 2 0 undeca 4 10 dien 8 one Organic Syntheses 81 171 doi 10 15227 orgsyn 081 0171 a href Template Cite journal html title Template Cite journal cite journal a CS1 maint multiple names authors list link CS1 maint numeric names authors list link Maliverney Christian Mulhauser Michel 2000 Hydroxybenzaldehydes Kirk Othmer Encyclopedia of Chemical Technology doi 10 1002 0471238961 0825041813011209 a01 ISBN 978 0 471 48494 3 Bassoli Angela Merlini Lucio Morini Gabriella 2002 Isovanillyl sweeteners From molecules to receptors Pure and Applied Chemistry 74 7 1181 1187 doi 10 1351 pac200274071181 ISSN 1365 3075 S2CID 53554546 Seo Eun Seong Lee Jin Ha Park Ji Young Kim Doman Han Ho Jae Robyt John F 2005 Enzymatic synthesis and anti coagulant effect of salicin analogs by using the Leuconostoc mesenteroides glucansucrase acceptor reaction Journal of Biotechnology 117 1 31 38 doi 10 1016 j jbiotec 2004 10 013 PMID 15831245 Retrieved from https en wikipedia org w index php title Salicyl alcohol amp oldid 1212208915, wikipedia, wiki, book, books, library,

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