2D Structure

3D Structure

α-Terpinene


Properties
PID PID00091
Mol. Weight 136.238 g/mol
LogP 2.17
Water solubility 0.00363 mol/L at 20 °C
Hydrogen Bond Donor 0
Hydrogen Bond Acceptor 0
Rotatable Bonds 1
XLogP3-AA 2.8

α-Terpinene

Identifiers
Formula C10H16
PubChem CID 7462
FEMA 3558
Flavor Profile Lemon
Smiles CC1=CC=C(CC1)C(C)C
InChl Key YHQGMYUVUMAZJR-UHFFFAOYSA-N
InChl InChI=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4,6,8H,5,7H2,1-3H3
CAS Registry Number 99-86-5
IUPAC Systematic Name 1-methyl-4-propan-2-ylcyclohexa-1,3-diene

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
Radix Aconiti KusnezoffiiCao Wu(草乌)Kusnezoff Monkshood RootHot,PungentLarge Intestine, StomachView Graph
Artemisia argyiAi Ye(艾叶)Argy Wormwood Leaf Equivalent plant: Artemisia monWarm,Pungent,BitterLung,Spleen,LiverView Graph
Chinese Star AniseBa Jiao Hui Xiang (八角茴香)Anisi Stellati FructusWarm, PungentLung, Spleen, StomachView Graph
Wild MintBo He (薄荷)Menthae Haplocalycis HerbaCool, PungentLiver, LungView Graph
Chuanxiong (Wallich Ligusticum) Equivalent plantChuan Xiong (川芎)Ligusticum chuanxiong HortWarm, PungentLung, Spleen, StomachView Graph
Zedoray RhizomeE Zhu (莪术)Curcumae RhizomaWarm, Pungent, BitterSpleen, LiverView Graph
Common Ginger Dried RhizomeGan Jiang (干姜)Zingiberis RhizomaHot, PungentLung, Spleen, Stomach, Heart, KidneyView Graph
Chinese Ligusticum Equivalent plant: Ligusticum jeGao Ben (藁本)Ligustici Rhizoma Et RadixWarm, PungentLung, Spleen, StomachView Graph
Cassiabarktree TwigGui Zhi (桂枝)Cinnamomi RamulusWarm, Pungent, SweetLung, Bladder, HeartView Graph
bark of Officinal magnoliaHou Pu(厚朴)Magnoliae Officinalis CortexWarm, Pungent, BitterSpleen, LiverView 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
Dahurian RhododendronMan Shan Hong (满山红)Rhododendri Daurici FoliumCold, Pungent, BitterLiver, Heart, LungView 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
Daucus carotaNan He Shi(南鹤虱)Wild Carrot FruitNeural, Bitter, PungentLungView Graph
Incised Notopterygium Equivalent plant: NotopteryQiang Huo(羌活)Notopterygii Rhizoma Et RadixWarm, Bitter, PungentSpleen, Large Intestine, Stomach, Gallbladder, Three EndView Graph
Green Tangerine PeelQing Pi (青皮)Citri Reticulatae Pericarpium VirideWarm, Pungent, BitterSpleen, LiverView Graph
CassiabarktreeRou Gui (肉桂)Cinnamomi CortexHot, Sweet, PungentLiver, Heart, Spleen, KidneyView Graph
Villous Amomum Equivalent plant: Amomum xanthioideSha Ren (砂仁)Amomi FructusWarm, PungentLung, Spleen, StomachView Graph
Common Japanese Clubmoss Equivalent plant: LycopodShen Jin Cao(伸筋草)Lycopodii HerbaWarm, Bitter, PungentLarge Intestine, StomachView Graph
Fresh Common GingerSheng Jiang (生姜)Zingiber Rhizoma RecensWarm, PungentLung, Spleen, StomachView Graph
Evodia rutaecarpaWu Zhu Yu(吴茱萸)Medicinal Evodia Equivalent plant: Evodia rutaecarPungent, bitter, hotLiver, spleen,stomachView Graph
Siebold Wildginger Equivalent plant: Asarum heteroXi Xin (细辛)Asari Radix Et RhizomaWarm, PungentLung, Spleen, StomachView Graph
Haichow ElsholtziaXiang Ru (香薷)Moslae HerbaMinor Warm,PungentLung, Spleen, StomachView Graph
Lily Magnolia Buds Equivalent plant: Magnolia liliXin Yi (辛夷)Magnoliae FlosWarm, PungentLung, Spleen, StomachView Graph
Aromatic TurmericYu Jin (郁金)Curcumae RadixCold, Pungent, BitterLiver, Heart, LungView Graph
Illicium difengpiDi Feng Pi(地枫皮)Difengpi Anisetree Equivalent plant: Illicium majuWarm,Slightly Pungent,PunkeryBladder,KidneyView Graph
Oriental Sweetgum ResinSu He Xiang (苏合香)StyraxWarm, PungentLung, Spleen, StomachView Graph

Pharmacological action

Alpha-Terpinene is an important natural flavouring compound present in various foods such as oranges, lime, oregano,and coriander and is mainly used to confer

pleasant odor to industrial fluids.

The Alpha-terpinene showed faster trypanocidal effect compared to chemotherapy.Alpha-terpinene was able to extend animal longevity, but showed no curative efcacy.

Alpha-terpinene from M. alternifolia is the one responsible for the trypanocidal effect. Alpha-terpinene associated with D.A. can be used as an alternative

treatment for T. evansi infection. Alpha-terpinene, have no direct antibacterial activity against the S. aureus 1199B strain and S. aureus 1199wild.the

Alpha-Terpinene tests did not show activity, being inefficient both in the direct action as well as in the potentiating action against antibacterials.

Alpha-Terpinene caused embryo and foetal oxicity when given to rats (by stomach tube) at doses of 60 mg/kg body weight/day and above on days 6-15 of pregnancy.

Chemotherapy associate with Alpha-terpinene showed a curative efcacy of 57.14%. The MIC of the essential oil and Alpha-Terpinene presented a value e" 1024 g/mL.



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. Lee J Y, Jung M Y. Effects and mechanisms of eugenol, isoeugenol, coniferylaldehyde and dihydroeugenol on the riboflavin-sensitized photooxidation of -terpinene in methanol[J]. Food chemistry, 2017, 220: 289-294.

2. Gomes-Carneiro M R, Viana M E S, Felzenszwalb I, & Paumgartten, F. J. (2005). Evaluation of -myrcene, -terpinene and (+)-and (?)--pinene in the Salmonella/microsome assay[J]. Food and chemical toxicology, 2005, 43(2): 247-252.

3. Baldissera M D, Grando T H, Souza C F, Gressler, L. T., Stefani, L. M., da Silva, A. S., & Monteiro, S. G. In vitro and in vivo action of terpinen-4-ol, -terpinene, and -terpinene against Trypanosoma evansi[J]. Experimental parasitology, 2016, 162: 43-48.

4. de Morais Oliveira-Tintino C D, Tintino S R, Limaverde P W, Figueredo, F. G., Campina, F. F., da Cunha, F. A., Coutinho, H. D. M. Inhibition of the essential oil from Chenopodium ambrosioides L. and -terpinene on the NorA efflux-pump of Staphylococcus aureus[J]. Food chemistry, 2018, 262: 72-77.

5. Limaverde P W, Campina F F, da Cunha F A B, Crispim, F. D., Figueredo, F. G., Lima, L. F., Balbino, V. Q. Inhibition of the TetK efflux-pump by the essential oil of Chenopodium ambrosioides L. and -terpinene against Staphylococcus aureus IS-58[J]. Food and Chemical Toxicology, 2017, 109: 957-961.

6. Comelli N A, Ponzi E N, Ponzi M I. Isomerization of -pinene, limonene, -terpinene, and terpinolene on sulfated zirconia[J]. Journal of the American Oil Chemists' Society, 2005, 82(7): 531-535.

7. Choi Y S, Jung M Y. Kinetic study on the singlet oxygen quenching activity of nordihydroguaiaretic acid (NDGA) using methylene blue sensitized photooxidation of -terpinene[J]. Food science and biotechnology, 2016, 25(5): 1333-1336.

8. Choi D S, Jung M Y. Protective activities of catechins on singlet oxygen induced photooxidation of -terpinene in methanol: Structure and singlet oxygen quenching activity relationship[J]. Food Science and Biotechnology, 2013, 22(1): 249-256.

9. Pluzhnikov V A, Kovtun G A. Radical chain mechanism of the oxidation of -terpinene by molecular oxygen[J]. Theoretical and Experimental Chemistry, 1994, 30(3): 117-119.

10. http://linkinghub.elsevier.com/retrieve/pii/S0278691597892939

11. Araujo I B, Souza C A M, De-Carvalho R R, Kuriyama, S. N., Rodrigues, R. P., Vollmer, R. S., Paumgartten, F. J. R. Study of the embryofoetotoxicity of -terpinene in the rat[J]. Food and chemical toxicology, 1996, 34(5): 477-482.

12. Bardyshev I I, Dontsova E P. The presence of -terpinene in the turpentines of various conifers[J]. Chemistry of Natural Compounds, 1969, 5(2): 106-107.

13. Shvydkiv O, J?hnisch K, Steinfeldt N, et al. Visible-light photooxygenation of -terpinene in a falling film microreactor[J]. Catalysis Today, 2018, 308: 102-118

14. Ronzani F, Costarramone N, Blanc S, Benabbou, A. K., Le Bechec, M., Pigot, T., Lacombe, S. Visible-light photosensitized oxidation of -terpinene using novel silica-supported sensitizers: Photooxygenation vs. photodehydrogenation[J]. Journal of catalysis, 2013, 303: 164-174.

15. https://en.wikipedia.org/wiki/Terpinene