2D Structure

3D Structure

l-Limonene


Properties
PID PID00125
Mol. Weight 136.238 g/mol
LogP 4.38
Water solubility 0.00339 mol/L at 20 °C
Hydrogen Bond Donor 0
Hydrogen Bond Acceptor 0
Rotatable Bonds 1
XLogP3-AA 3.4

l-Limonene

Identifiers
Formula C10H16
PubChem CID 439250
FEMA /
Flavor Profile None
Smiles C=C(C)[C@@H]1CC=C(C)CC1
InChl Key XMGQYMWWDOXHJM-SNVBAGLBSA-N
InChl InChI=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4,10H,1,5-7H2,2-3H3/t10-/m1/s1
CAS Registry Number 5989-54-8
IUPAC Systematic Name (4S)-1-methyl-4-prop-1-en-2-ylcyclohexene

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
Artemisia argyiAi Ye(艾叶)Argy Wormwood Leaf Equivalent plant: Artemisia monWarm,Pungent,BitterLung,Spleen,LiverView Graph
Dahurian AngelicaBai Zhi(白芷)Angelicae Dahuricae RadixWarm, PungentLung, Spleen, StomachView Graph
Wild MintBo He (薄荷)Menthae Haplocalycis HerbaCool, PungentLiver, LungView Graph
Piper cubebaBi Cheng Qie(荜澄茄)Cubeba PepperWarm, PungentLung, Spleen, StomachView Graph
BetenutpalmBing Lang (槟榔)Arecae SemenWarm, Bitter, PungentLarge Intestine, StomachView Graph
Chinese Thorowax Equivalent plant: Bupleurum scorzChai Hu(柴胡)Bupleuri RadixMinor cold, Pungent, BitterLiver, Gallbladder, LungView Graph
Dichroa febrifugaChang Shan(常山)Antifebrile DichroaCold,Pungent,BitterLung,Liver,HeartView Graph
Chuanxiong (Wallich Ligusticum) Equivalent plantChuan Xiong (川芎)Ligusticum chuanxiong HortWarm, PungentLung, Spleen, StomachView Graph
Round Cardamon FruitDou Kou (豆蔻)Amomi Fructus RotundusWarm, Pungent,Spleen, Lung, StomachView Graph
Divaricate SaposhnikoviaFang Feng (防风)Saposhnikoviae RadixWarm, Pungent, SweetLung, Bladder, HeartView Graph
Fleshfingered CitronFo Shou (佛手)Citri Sarcodactylis FructusWarm, Pungent, Sour, BitterLung, Spleen, Stomach, Liver, KidneyView Graph
Chinese Nardostachys Equivalent plant: NardostachyGan Song(甘松)Nardostachyos Radix Et RhizomaWarm, Pungent, SweetLung, Bladder, HeartView Graph
Lesser GalangalGao Liang Jiang (高良姜)Alpiniae Officinarum RhizomaHot,PungentLarge Intestine, StomachView Graph
Hypericum perforatum L.Guan Ye Jin Si Tiao(贯叶金丝桃)Hyperici Perforati HerbaCold, PungentLungView Graph
Cablin PotchouliGuang Huo Xiang (广藿香)Pogostemonis HerbaMinor Warm,PungentLung, Spleen, StomachView Graph
Cassiabarktree TwigGui Zhi (桂枝)Cinnamomi RamulusWarm, Pungent, SweetLung, Bladder, HeartView Graph
Black PepperHu Jiao (胡椒)Piperis FructusHot,PungentLarge Intestine, StomachView Graph
Bunge Pricklyash Equivalent plant: Zanthoxylum schHua Jiao (花椒)Zanthoxyli PericarpiumWarm,PungentSpleen, Stomach, Kidney, LungView Graph
Exocarpium Citri grandisHua Ju Hong(化橘红)Pummelo PeelMild,BitterLiverView Graph
Asiatic PennywortJi Xue Cao (积雪草)Centellae HerbaCold, Sweet, BitterLiver, Spleen, KidneyView Graph
Brassica junceaJie Zi(芥子)India Mustard SeedWarm, PungentLung, Spleen, StomachView Graph
Fineleaf SchizonepetaJing Jie (荆芥)Schizonepetae HerbaMinor Warm, PungentLung, LiverView Graph
Exocarpium Citri RubrumJu Hong (橘红)Citri Exocarpium RubrumWarm, Pungent, BitterSpleen, LiverView Graph
Herba GlechomaeLian Qian Cao(连钱草)Longtube Ground Ivy HerbCold, Bitter, PungentBladder, Spleen, Liver,StomachView Graph
Chinese Ephedra Equivalent plant: Ephedra equisetiMa Huang (麻黄)Ephedrae HerbaWarm, Pungent, Slightly BitterLung, BladderView Graph
Threeleaf Chastetree Fruit Equivalent plant: VitexMan Jing Zi (蔓荆子)Viticis FructusMinor cold, Pungent, BitterLiver, Gallbladder, LungView Graph
Folium Viticis NegundoMu Jing Ye(牡荆叶)Hempleaf Negundo Chastetree LeafNeural, Bitter, PungentLungView Graph
Euphorbia lathyrisQian Jin Zi(千金子)Caper Euphorbia SeedWarm,PungentSpleen, Stomach, Kidney, LungView Graph
rhizome of Obscured HomalomenaQian Nian Jian(千年健)Homalomenae RhizomaWarm, Bitter, PungentSpleen, Large Intestine, Stomach, Gallbladder, Three EndView Graph
Celery WormwoodQing Hao(青蒿)Artemisiae Annuae HerbaCold, Bitter, PungentLiver, bladderView Graph
Green Tangerine PeelQing Pi (青皮)Citri Reticulatae Pericarpium VirideWarm, Pungent, BitterSpleen, LiverView Graph
Common NutmegRou Dou Kou(肉豆蔻)Myristicae SemenWarm, PungentLung, Spleen, StomachView Graph
CassiabarktreeRou Gui (肉桂)Cinnamomi CortexHot, Sweet, PungentLiver, Heart, Spleen, KidneyView Graph
Frankincense, OlibanumRu Xiang (乳香)OlibanumWarm,Bitter, PungentSpleen, LungView Graph
Villous Amomum Equivalent plant: Amomum xanthioideSha Ren (砂仁)Amomi FructusWarm, PungentLung, Spleen, StomachView Graph
Galanga ResurrectionlilyShan Nai (山柰)Kaempferiae RhizomaWarm, Pungent,StomachView Graph
Fresh Common GingerSheng Jiang (生姜)Zingiber Rhizoma RecensWarm, PungentLung, Spleen, StomachView Graph
Oriental Sweetgum ResinSu He Xiang (苏合香)StyraxWarm, PungentLung, Spleen, StomachView Graph
SandalwoodTan Xiang(檀香)Santali Albi LignumWarm, PungentLung, Spleen, StomachView Graph
Combined SpicebushWu Yao(乌药)Linderae RadixWarm, PungentLung, Spleen, StomachView Graph
Siebold Wildginger Equivalent plant: Asarum heteroXi Xin (细辛)Asari Radix Et RhizomaWarm, PungentLung, Spleen, StomachView Graph
Wilson CitronXiang Yuan(香橼)Citri FructusWarm, Pungent, Sour, Slightly BitterLung, Spleen, LiverView Graph
Fennel FruitXiao Hui Xiang (小茴香)Foeniculi FructusWarm, PungentLung, Spleen, StomachView Graph
Common GoldenrodYi Zhi Huang Hua(一枝黄花)Solidaginis HerbaCool, Bitter, PungentLiver, LungView Graph
Apple MintYu Xian Cao(鱼腥草)Houttuyniae HerbaCold, PungentLungView Graph
Aromatic TurmericYu Jin (郁金)Curcumae RadixCold, Pungent, BitterLiver, Heart, LungView Graph
Seville Ora nge Unripe Fruit Equivalent plant: PoZhi Ke(枳壳)Aurantii FructusCold, Sour, Bitter, PungentSpleen, StomachView Graph
Seville Orange Young Fruit Equivalent plant: CitruZhi Shi(枳实)Aurantii Fructus ImmaturusCold, Sour, Bitter, PungentSpleen, StomachView Graph
Perilla frutescens var. argutaZi Su(紫苏叶)Common Perilla Equivalent plant: Perilla frutescenWarm, PungentLung, Spleen, StomachView Graph

Pharmacological action

L-isomer is found in mint oils and has a piny, turpentine-like odor.



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. Singh P, Shukla R, Prakash B,Ashok Kumar,Shubhra Singh ,Prashant Kumar Mishra,Nawal Kishore Dubey. Chemical profile, antifungal, antiaflatoxigenic and antioxidant activity of Citrus maxima Burm. and Citrus sinensis (L.) Osbeck essential oils and their cyclic monoterpene, DL-limonene[J]. Food and Chemical Toxicology, 2010, 48(6): 1734-1740.

2. Bouwmeester, H. J., Konings, M. C., Gershenzon, J., Karp, F., Croteau, R. Cytochrome P-450 dependent (+)-limonene-6-hydroxylation in fruits of caraway (Carum carvi)[J]. Phytochemistry, 1999, 50(2): 243-248.

3. https://en.wikipedia.org/wiki/Limonene