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Menthol

from peppermint or mint oils flavor and local anesthetic. Product of hydrolysis of menthol acetate, or substrate of acyltransferase. Menthol has eight possible isomers but the characteristic peppermint odour and the typical cooling/refreshing effect are only attributed to l-menthol

General

Type : Natural, Flavor

Chemical_Nomenclature : 5-methyl-2-propan-2-ylcyclohexan-1-ol

Canonical SMILES : CC1CCC(C(C1)O)C(C)C

InChI : InChI=1S\/C10H20O\/c1-7(2)9-5-4-8(3)6-10(9)11\/h7-11H,4-6H2,1-3H3

InChIKey : NOOLISFMXDJSKH-UHFFFAOYSA-N

Other name(s) : dl-Menthol  ||  1490-04-6  ||  2-Isopropyl-5-methylcyclohexanol  ||  SCHEMBL4612  ||  CHEMBL256087

MW : 156.26

Formula : C10H20O

CAS_number : 15356-70-4

PubChem : 1254

UniChem : NOOLISFMXDJSKH-UHFFFAOYSA-N

Target

Structures : No structure

Families : Hormone-sensitive_lipase_like, Fungal_carboxylesterase_lipase

References (11)

Title : Engineering a Bacillus subtilis esterase for selective hydrolysis of d, l-menthyl acetate in an organic solvent-free system - Qiao_2023_RSC.Adv_13_10468
Author(s) : Qiao J , Yang D , Feng Y , Wei W , Liu X , Zhang Y , Zheng J , Ying X
Ref : RSC Adv , 13 :10468 , 2023
Abstract :
PubMedSearch : Qiao_2023_RSC.Adv_13_10468
PubMedID: 37021103
Gene_locus related to this paper: 9baci-a0a2m8sv47

Title : DES-Based Biocatalysis as a Green Alternative for the l-menthyl Ester Production Based on l-menthol Acylation - Ion_2022_Molecules_27_
Author(s) : Ion S , Olanescu F , Teodorescu F , Tincu R , Gheorghe D , Parvulescu VI , Tudorache M
Ref : Molecules , 27 : , 2022
Abstract :
PubMedSearch : Ion_2022_Molecules_27_
PubMedID: 36014511

Title : Rational Design for Enhanced Acyltransferase Activity in Water Catalyzed by the Pyrobaculum calidifontis VA1 Esterase - Staudt_2021_Microorganisms_9_1790
Author(s) : Staudt A , Terholsen H , Kaur J , Muller H , Godehard SP , Itabaiana I, Jr. , Leal ICR , Bornscheuer UT
Ref : Microorganisms , 9 :1790 , 2021
Abstract :
PubMedSearch : Staudt_2021_Microorganisms_9_1790
PubMedID: 34442869
Gene_locus related to this paper: pyrca-PCEST

Title : Recent Insights and Future Perspectives on Promiscuous Hydrolases\/Acyltransferases - Muller_2021_ACS.Catal_11_14906
Author(s) : Muller H , Terholsen H , Godehard SP , Badenhorst CPS , Bornscheuer UT
Ref : ACS Catal , 11 :12864 , 2021
Abstract :
PubMedSearch : Muller_2021_ACS.Catal_11_14906
PubMedID:

Title : Cutinases as stereoselective catalysts: Specific activity and enantioselectivity of cutinases and lipases for menthol and its analogs - Su_2020_Enzyme.Microb.Technol_133_109467
Author(s) : Su A , Kiokekli S , Naviwala M , Shirke AN , Pavlidis IV , Gross RA
Ref : Enzyme Microb Technol , 133 :109467 , 2020
Abstract :
PubMedSearch : Su_2020_Enzyme.Microb.Technol_133_109467
PubMedID: 31874689
Gene_locus related to this paper: humin-cut , canar-LipB , humla-1lipa , rhimi-lipas

Title : Determinants and prediction of esterase substrate promiscuity patterns - Martinez-Martinez_2018_ACS.Chem.Biol_13_225
Author(s) : Martinez-Martinez M , Coscolin C , Santiago G , Chow J , Stogios PJ , Bargiela R , Gertler C , Navarro-Fernandez J , Bollinger A , Thies S , Mendez-Garcia C , Popovic A , Brown G , Chernikova TN , Garcia-Moyano A , Bjergah GE , Perez-Garcia P , Hai T , Del Pozo MV , Stokke R , Steen IH , Cui H , Xu X , Nocek BP , Alcaide M , Distaso M , Mesa V , Pelaez AI , Sanchez J , Buchholz PCF , Pleiss J , Fernandez-Guerra A , Glockner FO , Golyshina OV , Yakimov MM , Savchenko A , Jaeger KE , Yakunin AF , Streit WR , Golyshin PN , Guallar V , Ferrer M
Ref : ACS Chemical Biology , 13 :225 , 2018
Abstract :
PubMedSearch : Martinez-Martinez_2018_ACS.Chem.Biol_13_225
PubMedID: 29182315
Gene_locus related to this paper: 9zzzz-a0a2k8jn75 , 9zzzz-a0a2k8jt94 , 9zzzz-a0a0g3fj44 , 9zzzz-a0a0g3fh10 , 9zzzz-a0a0g3fh03 , 9bact-a0a1s5qkj8 , 9zzzz-a0a0g3feh5 , 9zzzz-a0a0g3fkz4 , 9zzzz-a0a0g3fh07 , 9zzzz-a0a0g3fh34 , 9zzzz-a0a0g3fh31 , 9bact-KY458167 , alcbs-q0vqa3 , 9bact-a0a1s5qki8 , 9zzzz-a0a0g3feq8 , 9zzzz-a0a0g3feh8 , 9zzzz-a0a0g3fh19 , 9bact-KY203037 , 9bact-a0a1s5ql22 , 9bact-a0a1s5qm34 , 9bact-KY203034 , 9bact-r9qzg0 , 9bact-a0a1s5qly8 , 9zzzz-a0a0g3fkz8 , 9zzzz-a0a0g3feg9 , 9zzzz-KY203033 , 9zzzz-a0a0g3fes4 , 9zzzz-a0a0g3fh42 , 9bact-a0a1s5qlx2 , 9zzzz-KY483651 , 9bact-a0a1s5qmh4 , 9zzzz-KY203032 , 9zzzz-EH87 , 9zzzz-a0a0g3fei1 , 9zzzz-a0a0g3fet2 , 9zzzz-KY483647 , 9zzzz-EH82 , 9zzzz-a0a0g3fe15 , 9bact-KY203031 , 9bact-t1w006 , 9zzzz-a0a0g3fet6 , 9bact-KY458164 , geoth-g8myf3 , 9bact-a0a1s5ql04 , 9gamm-a0a1y0ihk7 , 9bact-a0a1s5qly6 , 9bact-a0a1s5qkg4 , 9bact-a0a1s5qkm4 , 9gamm-s5tv80 , 9gamm-a0a0c4zhg2 , 9zzzz-t1b379 , 9gamm-KY483646 , 9bact-KY458160 , 9zzzz-a0a0g3fj57 , 9gamm-s5t8349 , 9arch-KY203036 , 9bact-KY458168 , 9zzzz-a0a0g3fes0 , 9zzzz-t1be47 , 9bact-KY458159 , 9zzzz-a0a0g3fh39 , 9bact-t1vzd5 , 9prot-EH41 , 9bact-Lip114 , alcbs-q0vt77 , 9bact-a0a1s5qke6 , 9bact-a0a1s5qkf3 , 9prot-SRP030024 , 9gamm-s5t532 , 9bact-a0a1s5qkl2 , 9bact-a0a1s5qkk8 , 9zzzz-KY203030 , 9zzzz-t1d4I7 , 9prot-KY019260 , 9bact-a0a1s5qm38 , 9arch-KY458161 , 9prot-KY010302 , 9zzzz-a0a0g3fl25 , 9actn-KY010298 , 9gamm-s5u059 , 9bact-a0a1s5qmi7 , 9bact-KY010297 , 9bact-KY483642 , 9bact-a0a1s5qkj1 , 9bact-KY010299 , 9bact-KY483648 , alcbs-q0vtl7 , 9bact-a0a1s5qf1 , 9bact-a0a1s5qkg0 , 9bact-a0a0h4tgu6 , 9bact-MilE3 , 9bact-LAE6 , 9alte-MGS-MT1 , 9bact-r9qzf7 , 9gamm-k0c6t6 , alcbs-q0vl36 , alcbs-q0vlq1 , alcbs-q0vq49 , bacsu-pnbae , canar-LipB , canan-lipasA , geost-lipas , marav-a1u5n0 , pseps-i7k8x5 , staep-GEHD , symth-q67mr3 , altma-s5cfn7 , cycsp-k0c2b8 , alcbs-q0vlk5 , 9bact-k7qe48 , 9bact-MGS-M1 , 9bact-MGS-M2 , 9bact-a0a0b5kns5 , 9zzzz-a0a0g3fej4 , 9zzzz-a0a0g3fj60 , 9zzzz-a0a0g3fej0 , 9zzzz-a0a0g3fj64 , 9bact-a0a0b5kc16 , 9zzzz-a0a0g3feg6 , 9zzzz-a0a0g3feu6

Title : Efficient kinetic resolution of (+\/-)-menthol by a lipase from Thermomyces lanuginosus - De Yan_2017_Biotechnol.Appl.Biochem_64_87
Author(s) : De Yan H , Li Q , Wang Z
Ref : Biotechnol Appl Biochem , 64 :87 , 2017
Abstract :
PubMedSearch : De Yan_2017_Biotechnol.Appl.Biochem_64_87
PubMedID: 26549685
Gene_locus related to this paper: humla-1lipa

Title : Biochemical studies on a versatile esterase that is most catalytically active with polyaromatic esters - Martinez-Martinez_2014_Microb.Biotechnol_7_184
Author(s) : Martinez-Martinez M , Lores I , Pena-Garcia C , Bargiela R , Reyes-Duarte D , Guazzaroni ME , Pelaez AI , Sanchez J , Ferrer M
Ref : Microb Biotechnol , : , 2014
Abstract :
PubMedSearch : Martinez-Martinez_2014_Microb.Biotechnol_7_184
PubMedID: 24418210
Gene_locus related to this paper: 9bacl-h6nd87

Title : pH memory of immobilized lipase for (+\/-)-menthol resolution in ionic liquid - Ren_2008_J.Agric.Food.Chem_56_2388
Author(s) : Ren MY , Bai S , Zhang DH , Sun Y
Ref : Journal of Agricultural and Food Chemistry , 56 :2388 , 2008
Abstract :
PubMedSearch : Ren_2008_J.Agric.Food.Chem_56_2388
PubMedID: 18338863

Title : Factors affecting the resolution of dl-menthol by immobilized lipase-catalyzed esterification in organic solvent - Wang_2002_J.Agric.Food.Chem_50_262
Author(s) : Wang DL , Nag A , Lee GC , Shaw JF
Ref : Journal of Agricultural and Food Chemistry , 50 :262 , 2002
Abstract :
PubMedSearch : Wang_2002_J.Agric.Food.Chem_50_262
PubMedID: 11782192

Title : A model of the pressure dependence of the enantioselectivity of Candida rugosalipase towards (+\/-)-menthol - Kahlow_2001_Protein.Sci_10_1942
Author(s) : Kahlow UH , Schmid RD , Pleiss J
Ref : Protein Science , 10 :1942 , 2001
Abstract :
PubMedSearch : Kahlow_2001_Protein.Sci_10_1942
PubMedID: 11567085
Gene_locus related to this paper: canru-1lipa