2D Structure

3D Structure

Menthone


Properties
PID PID00126
Mol. Weight 154.253 g/mol
LogP 3.05
Water solubility 0.0017 mol/L at 20 °C
Hydrogen Bond Donor 0
Hydrogen Bond Acceptor 1
Rotatable Bonds 1
XLogP3-AA 2.7

Menthone

Identifiers
Formula C10H18O
PubChem CID 26447
FEMA 2667
Flavor Profile Slight Peppermint Odor, Bitter; Green, Fresh, Mint
Smiles CC(C)[C@@H]1CC[C@@H](C)CC1=O
InChl Key NFLGAXVYCFJBMK-BDAKNGLRSA-N
InChl InChI=1S/C10H18O/c1-7(2)9-5-4-8(3)6-10(9)11/h7-9H,4-6H2,1-3H3/t8-,9+/m1/s1
CAS Registry Number 89-80-5, 14073-97-3
IUPAC Systematic Name (2S,5R)-5-methyl-2-propan-2-ylcyclohexan-1-one

Organ Location Map/System Distribution of Pungent Flavor Compounds’ Targets


Note: Known Targets (Gene) from 6952 literatures, DrugBank (http://www.drugbank.ca/), STITCH (http://stitch.embl.de/), ChEMBL (https://www.ebi.ac.uk/chembl/), Therapeutic Target Database (http://bidd.nus.edu.sg/group/ttd/), and Comparative Toxicogenomics Database (CTD, http://ctdbase.org/)


Related Pungent TCM

English Name Pinyin Name (Chinese Name) Latin Name Properties in TCM merdians View Graph
Wild MintBo He (薄荷)Menthae Haplocalycis HerbaCool, PungentLiver, LungView Graph
Chinese Thorowax Equivalent plant: Bupleurum scorzChai Hu(柴胡)Bupleuri RadixMinor cold, Pungent, BitterLiver, Gallbladder, LungView Graph
bark of Officinal magnoliaHou Pu(厚朴)Magnoliae Officinalis CortexWarm, Pungent, BitterSpleen, LiverView Graph
Asiatic PennywortJi Xue Cao (积雪草)Centellae HerbaCold, Sweet, BitterLiver, Spleen, KidneyView Graph
Fineleaf SchizonepetaJing Jie (荆芥)Schizonepetae HerbaMinor Warm, PungentLung, LiverView Graph
Herba SchizonepetaeJing Jie Sui (荆芥穗)Schizonepetae SpicaWarm, PungentLung, Spleen, StomachView Graph
Bush RedpepperLa Jiao (辣椒)Capsici FructusHot, PungentLung, Spleen, Stomach, Heart, KidneyView Graph
Chinese Ephedra Equivalent plant: Ephedra equisetiMa Huang (麻黄)Ephedrae HerbaWarm, Pungent, Slightly BitterLung, BladderView Graph
Bugbane Equivalent plant: Cimicifuga dahurica, CiSheng Ma(升麻)Cimicifugae RhizomaCold, Sweet, PungentLung, Spleen, Large Intestine, StomachView Graph
Fresh Common GingerSheng Jiang (生姜)Zingiber Rhizoma RecensWarm, PungentLung, Spleen, StomachView Graph
Siebold Wildginger Equivalent plant: Asarum heteroXi Xin (细辛)Asari Radix Et RhizomaWarm, PungentLung, Spleen, StomachView Graph
Paniculate SwallowwortXu Chang Qing(徐长卿)Cynanchi Paniculati Radix Et RhizomaWarm, PungentLung, Spleen, StomachView Graph
Tokyo VioletZi Hua Di Ding (紫花地丁)Peucedani Decursivi RadixCold, Pungent, BitterLiver, Heart, LungView Graph
Alpinia katsumadaiCao Dou Kou(草豆蔻)Katsumada GalangalWarm,PungentSpleen, Stomach, Kidney, LungView Graph
Haichow ElsholtziaXiang Ru (香薷)Moslae HerbaMinor Warm,PungentLung, Spleen, StomachView Graph
Perilla frutescens var. argutaZi Su(紫苏叶)Common Perilla Equivalent plant: Perilla frutescenWarm, PungentLung, Spleen, StomachView Graph

Pharmacological action

Menthone is a constituent of the essential oils of pennyroyal, peppermint, Mentha arvensis, Pelargonium geraniums, and others. In most essential oils, it is a minor compound. This is the cause for the fact that it was first synthesized by oxidation of menthol in 1881 before it was found in essential oils in 1891.



Note: Click anywhere in the blank, you can drag the whole dynamic diagram. Click on a node, you can drag his location to see it more clearly. The blue circle represents pharmacology, toxicology, or daily use. Orange hexagon represents the pungent compounds.

References

1.Bhatia K S, Singh J. Mechanism of transport enhancement of LHRH through porcine epidermis by terpenes and iontophoresis: permeability and lipid extraction studies[J]. Pharmaceutical research, 1998, 15(12): 1857-1862.

2.Dambolena J S, Lpez A G, Cnepa M C, et al. Inhibitory effect of cyclic terpenes (limonene, menthol, menthone and thymol) on Fusarium verticillioides MRC 826 growth and fumonisin B1 biosynthesis[J]. Toxicon, 2008, 51(1): 37-44.

3.Xue J, Li H, Deng X, et al. L-Menthone confers antidepressant-like effects in an unpredictable chronic mild stress mouse model via NLRP3 inflammasome-mediated inflammatory cytokines and central neurotransmitters[J]. Pharmacology Biochemistry and Behavior, 2015, 134: 42-48.

4.Coleman W K, Lonergan G, Silk P. Potato Sprout Growth Suppression by Menthone and Neomenthol, Volatile Oil Components ofMinthostachys, Satureja, Bystropogon, andMentha Species[J]. American journal of potato research, 2001, 78(5): 345-354.

5.Hu G, Yuan X, Zhang S, et al. Research on choleretic effect of menthol, menthone, pluegone, isomenthone, and limonene in DanShu capsule[J]. International immunopharmacology, 2015, 24(2): 191-197.

6.https://en.wikipedia.org/wiki/Menthone