(-)-Menthol (BioCAD00000000071)

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Metabolite Card

Formula: C10H20O (156.1514)
SMILES: CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O

Synonyms [en]

(-)-menthol; l-Menthol; Levomenthol; levomentol; Menthacamphor; U.S.P. Menthol

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

(-)-Menthol. 数据之源，洞见之始. SMRUCC genomics institute, a synthetic life researcher from China. https://biocad_registry.innovation.ac.cn/s/(-)-arctiin (retrieved 2026-01-03) (CAD Registry RN: BioCAD00000000071). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

Menthol is an alcohol produced from mint oils or prepared synthetically. Menthol is a covalent organic compound made synthetically or obtained from peppermint or other mint oils. It is a waxy, crystalline substance, clear or white in color, which is solid at room temperature and melts slightly above. The main form of menthol occurring in nature is (-)-menthol, which is assigned the (1R,2S,5R) configuration. Menthol has local anesthetic and counterirritant qualities, and it is widely used to relieve minor throat irritation.

Extracellular Membrane
Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 114376-98-6
  • CAS Registry Number: 15356-70-4
  • CAS Registry Number: 2216-51-5
  • CAS Registry Number: 89-78-1
  • CAS Registry Number: 98167-53-4
  • PubChem: 11228933
  • PubChem: 16666
  • ChEBI: ChEBI:15409
  • HMDB: HMDB0003352
  • LipidMaps: LMPR0102090001
  • KEGG: C00400
  • BioCyc: --MENTHOL
  • Wikipedia: Menthol
  • DrugBank: DB00825
  • RefMet: RM0135317
  • MoNA: JP002472
  • MoNA: JP006346
  • MoNA: PS043602
  • MoNA: VF-NPL-QEHF011692
  • MoNA: VF-NPL-QEHF011693
  • MoNA: VF-NPL-QEHF011694
  • MoNA: VF-NPL-QEHF011695
  • MoNA: VF-NPL-QEHF011696
  • MoNA: VF-NPL-QEHF011697
  • MoNA: VF-NPL-QEHF011698
  • MoNA: VF-NPL-QEHF011699
  • MoNA: VF-NPL-QEHF011700
  • MoNA: VF-NPL-QEHF011701
  • MoNA: VF-NPL-QEHF011702
  • MoNA: VF-NPL-QEHF011703
  • MoNA: VF-NPL-QEHF011704
  • MoNA: VF-NPL-QEHF011705
  • MoNA: VF-NPL-QEHF011706
  • Metlin: METLIN_41062
  • Coconut NaturalProduct: CNP0243697.6
  • Coconut NaturalProduct: CNP0362039.1
  • Coconut NaturalProduct: CNP0367585.1
  • Coconut NaturalProduct: CNP0367585.2

Class / Ontology

Metabolic Network
ID EC Number Name
KEGG:R02177 1.1.1.207 (-)-menthol:NADP+ oxidoreductase
KEGG:R02178 1.14.13.46 (-)-menthol,NADPH:oxygen oxidoreductase (8-hydroxylating)
KEGG:R02179 2.4.1.127 UDPglucose:(-)-menthol O-beta-D-glucosyltransferase
KEGG:R08530 2.3.1.69 acetyl-CoA:monoterpenol O-acetyltransferase
Rhea:RHEA:11521 2.4.1.127 (−)-menthol + UDP-α-D-glucose => (−)-menthyl β-D-glucoside + UDP + H+
Rhea:RHEA:11522 2.4.1.127 (−)-menthyl β-D-glucoside + UDP + H+ => (−)-menthol + UDP-α-D-glucose
Rhea:RHEA:11523 2.4.1.127 (−)-menthol + UDP-α-D-glucose <=> (−)-menthyl β-D-glucoside + UDP + H+
Rhea:RHEA:11649 1.14.13.46 (−)-menthol + NADPH + O2 + H+ => 1,4-menthane-3,8-diol + NADP+ + H2O
Rhea:RHEA:11650 1.14.13.46 1,4-menthane-3,8-diol + NADP+ + H2O => (−)-menthol + NADPH + O2 + H+
Rhea:RHEA:11651 1.14.13.46 (−)-menthol + NADPH + O2 + H+ <=> 1,4-menthane-3,8-diol + NADP+ + H2O
Rhea:RHEA:13918 1.1.1.207 (−)-menthol + NADP+ => (1R,4S)-menthone + NADPH + H+
Rhea:RHEA:13919 1.1.1.207 (1R,4S)-menthone + NADPH + H+ => (−)-menthol + NADP+
Rhea:RHEA:13920 1.1.1.207 (−)-menthol + NADP+ <=> (1R,4S)-menthone + NADPH + H+
BioCyc:--MENTHOL-MONOOXYGENASE-RXN 1.14.13.46 --MENTHOL + OXYGEN-MOLECULE + NADPH + PROTON --> PARA-MENTHANE-38-DIOL + WATER + NADP
BioCyc:2.4.1.127-RXN 2.4.1.127 CPD-12575 + --MENTHOL --> CPD-1910 + UDP + PROTON
BioCyc:--MENTHOL-DEHYDROGENASE-RXN 1.1.1.207 PROTON + CPD-1909 + NADPH --> NADP + --MENTHOL
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Organism Source

Taxonomy Source

  1. Aconitum leucostomum [ncbi taxid: 632164]
  2. Actaea dahurica [ncbi taxid: 64029]
  3. Actaea heracleifolia [ncbi taxid: 64034]
  4. Actaea simplex [ncbi taxid: 64042]
  5. Agrimonia pilosa [ncbi taxid: 74656]
  6. Akebia quinata [ncbi taxid: 13331]
  7. Akebia trifoliata [ncbi taxid: 155132]
  8. Amomum longiligulare [ncbi taxid: ]
  9. Amomum villosum [ncbi taxid: ]
  10. Amomum xanthioides [ncbi taxid: ]
  11. Anarsia lineatella [ncbi taxid: 1101080]
  12. Apollonias barbujana [ncbi taxid: ]
  13. Aquilegia ecalcarata [ncbi taxid: 46965]
  14. Artemisia argyi [ncbi taxid: 259893]
  15. Artemisia dracunculus [ncbi taxid: 72341]
  16. Artemisia hanseniana [ncbi taxid: ]
  17. Artemisia montana [ncbi taxid: 669134]
  18. Artemisia princeps [ncbi taxid: 223870]
  19. Artemisia spp. [ncbi taxid: ]
  20. Atractylodes macrocephala [ncbi taxid: 265785]
  21. Blumea mollis [ncbi taxid: 119169]
  22. Capsicum annuum [ncbi taxid: 4072]
  23. Ceanothus velutinus [ncbi taxid: 54785]
  24. Centranthus longiflorus ssp. longiflorus [ncbi taxid: ]
  25. Chlorophytum borivilianum [ncbi taxid: 503355]
  26. Cimicifuga foetida [ncbi taxid: ]
  27. Dipterocarpus dyeri [ncbi taxid: 340441]
  28. Elsholtzia ciliata [ncbi taxid: 662901]
  29. Eremophila oppositifolia [ncbi taxid: 2652586]
  30. Fragaria vesca [ncbi taxid: 57918]
  31. Garcinia scortechinii [ncbi taxid: 180116]
  32. Gardenia tubifera [ncbi taxid: 1240870]
  33. Glechoma hederacea [ncbi taxid: 28509]
  34. Glechoma longituba [ncbi taxid: 516071]
  35. Helianthus annuus [ncbi taxid: 4232]
  36. Homo sapiens [ncbi taxid: 9606]
  37. Ipomoea cairica [ncbi taxid: 129201]
  38. Isodon lophanthoides [ncbi taxid: 204133]
  39. Kopsia grandifolia [ncbi taxid: 1750995]
  40. Lasianthus fordii [ncbi taxid: 1406743]
  41. Ledebouria socialis [ncbi taxid: 34191]
  42. Leonurus heterophyllus [ncbi taxid: ]
  43. Ligusticum jeholense [ncbi taxid: 49553]
  44. Ligusticum sinense [ncbi taxid: ]
  45. Ligusticum tenuissimum [ncbi taxid: ]
  46. Lycopus europaeus [ncbi taxid: 260603]
  47. Mentha aquatica [ncbi taxid: 190902]
  48. Mentha arvensis [ncbi taxid: 292239]
  49. Mentha canadensis [ncbi taxid: 294733]
  50. Mentha piperita [ncbi taxid: ]
  51. Mentha spicata [ncbi taxid: 29719]
  52. Mentha spp. [ncbi taxid: ]
  53. Mentha x piperita [ncbi taxid: 34256]
  54. Mentha x piperita L. [ncbi taxid: ]
  55. Mosla chinensis [ncbi taxid: 516065]
  56. Ocimum basilicum [ncbi taxid: 39350]
  57. Paederia scandens [ncbi taxid: 284589]
  58. Panax innovans [ncbi taxid: ]
  59. Penicillium cinerascens [ncbi taxid: 70096]
  60. Perilla frutescens [ncbi taxid: 48386]
  61. Persea mexicana [ncbi taxid: ]
  62. Pinellia ternata [ncbi taxid: 199225]
  63. Platycladus orientalis [ncbi taxid: 58046]
  64. Rhodobacter sphaeroides [ncbi taxid: ]
  65. Schizonepeta tenuifolia [ncbi taxid: 2849020]
  66. Schizonepeta tenuisfolia [ncbi taxid: ]
  67. Scutellaria barbata [ncbi taxid: 396367]
  68. Senna alexandrina [ncbi taxid: 72402]
  69. Sordaria araneosa [ncbi taxid: 573841]
  70. Stigmatella aurantiaca DW4/3-1 [ncbi taxid: 378806]
  71. Thymus quinquecostatus [ncbi taxid: 228974]
  72. Thymus vulgaris [ncbi taxid: 49992]
  73. Vitex negundo [ncbi taxid: 361442]
  74. Zanthoxylum bungeanum [ncbi taxid: 328401]
  75. Zanthoxylum piperitum [ncbi taxid: 354529]
  76. Zanthoxylum schinifolium [ncbi taxid: 354530]

Pathway Synthetic

pathway id name
BioCyc:META_PWY-3061 menthol biosynthesis
PlantCyc:PLANT_PWY-3061 menthol biosynthesis
PlantCyc:REDSAGE_PWY-3061 menthol biosynthesis
PlantCyc:ROSEMARY_PWY-3061 menthol biosynthesis
Reactome:R-HSA-9709957 Sensory Perception
Reactome:R-HSA-381753 Olfactory Signaling Pathway
View All Pathways