2D Structure

3D Structure

α-Terpineol


Properties
PID PID00018
Mol. Weight 154.253 g/mol
LogP 2.17
Water solubility In water, 7100 mg/L at 25 °C
Hydrogen Bond Donor 1
Hydrogen Bond Acceptor 1
Rotatable Bonds 1
XLogP3-AA 1.8

α-Terpineol

Identifiers
Formula C10H18O
PubChem CID 17100
FEMA 3045
Flavor Profile Lime (Distilled), Peach, Floral (Lilac) Flavor, Sweet, Lime Taste,Lilac, Floral, Sweet
Smiles CC1=CCC(C(C)(C)O)CC1
InChl Key WUOACPNHFRMFPN-UHFFFAOYSA-N
InChl InChI=1S/C10H18O/c1-8-4-6-9(7-5-8)10(2,3)11/h4,9,11H,5-7H2,1-3H3
CAS Registry Number 98-55-5, 8000-41-7, 8006-39-1
IUPAC Systematic Name 2-(4-methylcyclohex-3-en-1-yl)propan-2-ol

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
Siebold Wildginger Equivalent plant: Asarum heteroXi Xin (细辛)Asari Radix Et RhizomaWarm, PungentLung, Spleen, StomachView Graph
Fresh Common GingerSheng Jiang (生姜)Zingiber Rhizoma RecensWarm, PungentLung, Spleen, StomachView Graph
Illicium difengpiDi Feng Pi(地枫皮)Difengpi Anisetree Equivalent plant: Illicium majuWarm,Slightly Pungent,PunkeryBladder,KidneyView Graph
Chinese Angelica Equivalent plant: PhlojodicarpusDang Gui (当归)Angelicae Sinensis RadixWarm,Pungent,SweetSpleen,Liver,HeartView Graph
Fructus GalangaeHong Dou Kou(红豆蔻 )Galanga Galangal FruitWarm,PungentSpleen, Stomach, Kidney, LungView Graph
Bunge Pricklyash Equivalent plant: Zanthoxylum schHua Jiao (花椒)Zanthoxyli PericarpiumWarm,PungentSpleen, Stomach, Kidney, LungView Graph
Lily Magnolia Buds Equivalent plant: Magnolia liliXin Yi (辛夷)Magnoliae FlosWarm, PungentLung, Spleen, StomachView Graph
Fortune Eupatorium Equivalent plant: Eupatorium fPei Lan(佩兰)Eupatorii HerbaNeural, PungentLung,Spleen,StomachView Graph
Siebold Wildginger Equivalent plant: Asarum heteroXi Xin (细辛)Asari Radix Et RhizomaWarm, PungentLung, Spleen, StomachView Graph
Chinese ClematisWei Ling Xian (威灵仙)Clematidis Radix Et RhizomaWarm, Pungent, SaltyBladderView Graph
Villous Amomum Equivalent plant: Amomum xanthioideSha Ren (砂仁)Amomi FructusWarm, PungentLung, Spleen, StomachView Graph
Haichow ElsholtziaXiang Ru (香薷)Moslae HerbaMinor Warm,PungentLung, Spleen, StomachView Graph
Wild MintBo He (薄荷)Menthae Haplocalycis HerbaCool, PungentLiver, LungView Graph
Wilson CitronXiang Yuan(香橼)Citri FructusWarm, Pungent, Sour, Slightly BitterLung, Spleen, LiverView Graph

Pharmacological action

Alpha-Terpineol is a fragrance ingredient used in decorative cosmetics, fine fragrances, shampoos, toilet soaps, and other toiletries as well as in non-cosmetic products such as household cleaners and detergents. Its use worldwide is in the region of 100–1000 metric tonnes per annum. Alpha terpineol, a volatile monoterpenoid alcohol, is a major component of the essential oil of many plants and has been reported to enhance the permeability of skin to lipid soluble compounds.Alpha-terpineol show a broad spectrum of antifungal activity against some citrus postharvest pathogens such as Penicillium italicum and Penicillium digitatum. Alpha-terpineol has been shown to possess antimicrobial and anti-biofilm activity. Alpha terpineol has been described to have anti-inflammatory, antibacterial and antifungal activities



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 Oliveira M G B, Brito R G, Santos P L, et al. α-Terpineol, a monoterpene alcohol, complexed with β-cyclodextrin exerts antihyperalgesic effect in animal model for fibromyalgia aided with docking study[J]. Chemico-biological interactions, 2016, 254: 54-62.

2 Gouveia D N, Costa J S, Oliveira M A, et al. α-Terpineol reduces cancer pain via modulation of oxidative stress and inhibition of iNOS[J]. Biomedicine & Pharmacotherapy, 2018, 105: 652-661.

3 S. Held, P. Schieberle, V. Somoza, Characterization of α-Terpineol as an anti-inflammatory component of orange juice by in vitro studies using Oral Buccal cells, J.Agric. Food Chem. 55 (2007) 8040–8046

4 de Oliveira M G B, Marques R B, de Santana M F, et al. α‐Terpineol reduces mechanical hypernociception and inflammatory response[J]. Basic & clinical pharmacology & toxicology, 2012, 111(2): 120-125.

5 Quintans-Júnior L J, Oliveira M G B, Santana M F, et al. α-Terpineol reduces nociceptive behavior in mice[J]. Pharmaceutical biology, 2011, 49(6): 583-586.

6 Ribeiro T P, Porto D L, Menezes C P, et al. Unravelling the cardiovascular effects induced by α‐terpineol: A role for the nitric oxide–cGMP pathway[J]. Clinical and Experimental Pharmacology and Physiology, 2010, 37(8): 811-816.

7 Moghimi M, Parvardeh S, Zanjani T M, et al. Protective effect of α-terpineol against impairment of hippocampal synaptic plasticity and spatial memory following transient cerebral ischemia in rats[J]. Iranian journal of basic medical sciences, 2016, 19(9): 960.

8 Parvardeh S, Moghimi M, Eslami P, et al. α-Terpineol attenuates morphine-induced physical dependence and tolerance in mice: role of nitric oxide[J]. Iranian journal of basic medical sciences, 2016, 19(2): 201.

9 Choi Y J, Sim W C, Choi H K, et al. α-Terpineol induces fatty liver in mice mediated by the AMP-activated kinase and sterol response element binding protein pathway[J]. Food and chemical toxicology, 2013, 55: 129-136.

10 Prakash B, Singh P, Goni R, et al. Efficacy of Angelica archangelica essential oil, phenyl ethyl alcohol and α-terpineol against isolated molds from walnut and their antiaflatoxigenic and antioxidant activity[J]. Journal of food science and technology, 2015, 52(4): 2220-2228.

11 Park M J, Gwak K S, Yang I, et al. Effect of citral, eugenol, nerolidol and α-terpineol on the ultrastructural changes of Trichophyton mentagrophytes[J]. Fitoterapia, 2009, 80(5): 290-296.

12 Park S N, Lim Y K, Freire M O, et al. Antimicrobial effect of linalool and α-terpineol against periodontopathic and cariogenic bacteria[J]. Anaerobe, 2012, 18(3): 369-372.

13 Zhou H, Tao N, Jia L. Antifungal activity of citral, octanal and α-terpineol against Geotrichum citri-aurantii[J]. Food Control, 2014, 37: 277-283.

14 Pinto E, Gonçalves M J, Oliveira P, et al. Activity of Thymus caespititius essential oil and α-terpineol against yeasts and filamentous fungi[J]. Industrial Crops and Products, 2014, 62: 107-112.

15 Nogueira M N M, Aquino S G, Junior C R, et al. Terpinen-4-ol and alpha-terpineol (tea tree oil components) inhibit the production of IL-1β, IL-6 and IL-10 on human macrophages[J]. Inflammation research, 2014, 63(9): 769-778.

16 Hassan S B, Gali-Muhtasib H, Göransson H, et al. Alpha terpineol: a potential anticancer agent which acts through suppressing NF-κB signalling[J]. Anticancer Research, 2010, 30(6): 1911-1919.

17 Mukherji R, Prabhune A. A new class of bacterial quorum sensing antagonists: glycomonoterpenols synthesized using linalool and alpha terpineol[J]. World Journal of Microbiology and Biotechnology, 2015, 31(6): 841-849.

18 Bhatia S P, Letizia C S, Api A M. Fragrance material review on alpha-terpineol[J]. Food and Chemical Toxicology, 2008, 46(11): S280-S285.

19 Madyastha K M, Srivatsan V. Biotransformations of α-terpineol in the rat: its effects on the liver microsomal cytochrome P-450 system[J]. Bulletin of environmental contamination and toxicology, 1988, 41(1): 17-25.

20 Caccioni D R L, Guizzardi M, Biondi D M, et al. Relationship between volatile components of citrus fruit essential oils and antimicrobial action on Penicillium digitatum and Penicillium italicum[J]. International Journal of Food Microbiology, 1998, 43(1-2): 73-79.

21 Daferera D J, Ziogas B N, Polissiou M G. GC-MS analysis of essential oils from some Greek aromatic plants and their fungitoxicity on Penicillium digitatum[J]. Journal of agricultural and food chemistry, 2000, 48(6): 2576-2581.

22 Droby S, Eick A, Macarisin D, et al. Role of citrus volatiles in host recognition, germination and growth of Penicillium digitatum and Penicillium italicum[J]. Postharvest Biology and Technology, 2008, 49(3): 386-396.

23 Linde J H, Combrinck S, Regnier T J C, et al. Chemical composition and antifungal activity of the essential oils of Lippia rehmannii from South Africa[J]. South African Journal of Botany, 2010, 76(1): 37-42.

24 Wuryatmo E, Klieber A, Scott E S. Inhibition of citrus postharvest pathogens by vapor of citral and related compounds in culture[J]. Journal of agricultural and food chemistry, 2003, 51(9): 2637-2640.

25 Wolken W A M, Tramper J, van der Werf M J. Toxicity of terpenes to spores and mycelium of Penicillium digitatum[J]. Biotechnology and bioengineering, 2002, 80(6): 685-690.