2D Structure

3D Structure

Isoborneol


Properties
PID PID00132
Mol. Weight 154.253 g/mol
LogP 1.99
Water solubility 0.00525 mol/L at 20 °C
Hydrogen Bond Donor 1
Hydrogen Bond Acceptor 1
Rotatable Bonds 0
XLogP3 2.7

Isoborneol

Identifiers
Formula C10H18O
PubChem CID 6321405
FEMA 2158
Flavor Profile Piney, Camphoraceous Odor; Camphor, Must
Smiles CC1(C)[C@@H]2CC[C@@]1(C)[C@H](O)C2
InChl Key DTGKSKDOIYIVQL-MRTMQBJTSA-N
InChl InChI=1S/C10H18O/c1-9(2)7-4-5-10(9,3)8(11)6-7/h7-8,11H,4-6H2,1-3H3/t7-,8-,10+/m1/s1
CAS Registry Number 507-70-0, 10334-13-1, 124-76-5, 16725-71-6
IUPAC Systematic Name (1R,3R,4R)-4,7,7-trimethylbicyclo[2.2.1]heptan-3-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
Artemisia argyiAi Ye(艾叶)Argy Wormwood Leaf Equivalent plant: Artemisia monWarm,Pungent,BitterLung,Spleen,LiverView Graph
Long PepperBi Ba (荜茇)Piperis Longi FructusHot,PungentLarge Intestine, StomachView Graph
Dryobalanops aromaticaBing Pian(冰片)BorneolMinor cold,Pungent,BitterLung,Spleen,HeartView Graph
Chinese Thorowax Equivalent plant: Bupleurum scorzChai Hu(柴胡)Bupleuri RadixMinor cold, Pungent, BitterLiver, Gallbladder, LungView Graph
Illicium difengpiDi Feng Pi(地枫皮)Difengpi Anisetree Equivalent plant: Illicium majuWarm,Slightly Pungent,PunkeryBladder,KidneyView Graph
Zedoray RhizomeE Zhu (莪术)Curcumae RhizomaWarm, Pungent, BitterSpleen, LiverView Graph
Divaricate SaposhnikoviaFang Feng (防风)Saposhnikoviae RadixWarm, Pungent, SweetLung, Bladder, HeartView Graph
Common Ginger Dried RhizomeGan Jiang (干姜)Zingiberis RhizomaHot, PungentLung, Spleen, Stomach, Heart, KidneyView Graph
Lesser GalangalGao Liang Jiang (高良姜)Alpiniae Officinarum RhizomaHot,PungentLarge Intestine, 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
Impatiens balsaminaJi Xing Zi(急性子)Garden Balsam SeedPungent,BitterLiver,HeartView 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
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
Cnidium monnieriShe Chuang Zi(蛇床子)Common CnidiumWarm,Pungent,BitterLung,Spleen,LiverView Graph
Fresh Common GingerSheng Jiang (生姜)Zingiber Rhizoma RecensWarm, 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
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
Chinese ClematisWei Ling Xian (威灵仙)Clematidis Radix Et RhizomaWarm, Pungent, SaltyBladderView Graph

Pharmacological action

Borneol is a bicyclic organic compound and a terpene derivative. The hydroxyl group in this compound is placed in an endo position. There are two different

enantiomers of borneol. Both d-(+)-borneol and l-(–)-borneol are found in nature.

Isoborneol 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.

Isoborneol, a monoterpene and a component of several plant essential oils, showed dual viricidal activity against herpes simplex virus 1 (HSV-1).

Both Borneolum (Chinese name Bingpian; dextrorotatory borneol) and Borneolum syntheticum (synthetic Bingpian; a mixture of optically inactive borneol and

isoborneol) have been used for medicinal purposes in Chinese traditional medicine.



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. https://en.wikipedia.org/wiki/Borneol

2. Armaka, M., Papanikolaou, E., Sivropoulou, A., Arsenakis, M. Antiviral properties of isoborneol, a potent inhibitor of herpes simplex virus type 1[J]. Antiviral research, 1999, 43(2): 79-92.

3. Farhat, A., Benmoussa, H., Bachoual, R., Nasfi, Z., Elfalleh, W., Romdhane, M., Bouajila, J. Efficiency of the optimized microwave assisted extractions on the yield, chemical composition and biological activities of Tunisian Rosmarinus officinalis L. essential oil[J]. Food and bioproducts processing, 2017, 105: 224-233.

4. Bhatia, S. P., McGinty, D., Letizia, C. S., Api, A. M. Fragrance material review on isoborneol[J]. Food and Chemical Toxicology, 2008, 46(11): S182-S184.

5. Seo, K. A., Kim, H., Ku, H. Y., Ahn, H. J., Park, S. J., Bae, S. K., Liu, K. H. The monoterpenoids citral and geraniol are moderate inhibitors of CYP2B6 hydroxylase activity[J]. Chemico-biological interactions, 2008, 174(3): 141-146.

6. Guo, X., Cui, M., Deng, M., Liu, X., Huang, X., Zhang, X., Luo, L.. Molecular differentiation of five Cinnamomum camphora chemotypes using desorption atmospheric pressure chemical ionization mass spectrometry of raw leaves[J]. Scientific reports, 2017, 7: 46579.

7. Sam, M., Vora, S., Malnic, B., Ma, W., Novotny, M. V., Buck, L. B. Neuropharmacology: Odorants may arouse instinctive behaviours[J]. Nature, 2001, 412(6843): 142.

8. Xiao-fei, J., Jia-li, Z., Yue-mei, Y., Law, F. C., Yan-jiang, Q., Mei-cun, Y. Preliminary study: biotransformation of borneol to camphor in mice, rats, and rabbits[J]. World Science and Technology, 2008, 10(3): 27-36.

9. Api, A. M., Belsito, D., Bhatia, S., Bruze, M., Calow, P., Dagli, M. L., Lalko, J. F. RIFM fragrance ingredient safety assessment, Isoborneol, CAS Registry Number 124-76-5[J]. Food and Chemical Toxicology, 2015, 84: S33-S41.

10. Silva‐Filho, J. C., Oliveira, N. N. P., Arcanjo, D. D., Quintans‐Júnior, L. J., Cavalcanti, S. C., Santos, M. R. V., Oliveira, A. P. Investigation of Mechanisms Involved in (−)‐Borneol‐Induced Vasorelaxant Response on Rat Thoracic Aorta[J]. Basic & clinical pharmacology & toxicology, 2012, 110(2): 171-177.

11. Li, Y. H., Sun, X. P., Zhang, Y. Q., Wang, N. S. The antithrombotic effect of borneol related to its anticoagulant property[J]. The American Journal of Chinese Medicine, 2008, 36(04): 719-727.

12. Tian, L. L., Zhou, Z., Zhang, Q., Sun, Y. N., Li, C. R., Cheng, C. H., Wang, S. Q. Protective effect of (±) isoborneol against 6-OHDA-induced apoptosis in SH-SY5Y cells[J]. Cellular Physiology and Biochemistry, 2007, 20(6): 1019-1032.

13. Liu, R., Zhang, L., Lan, X., Li, L., Zhang, T. T., Sun, J. H., & Du, G. H. Protection by borneol on cortical neurons against oxygen-glucose deprivation/reperfusion: involvement of anti-oxidation and anti-inflammation through nuclear transcription factor κappaB signaling pathway[J]. Neuroscience, 2011, 176: 408-419.

14. Park, T. J., Park, Y. S., Lee, T. G., Ha, H., Kim, K. T. . Inhibition of acetylcholine-mediated effects by borneol[J]. Biochemical pharmacology, 2003, 65(1): 83-90.

15. Granger R E, Campbell E L, Johnston G A R. (+)-And (−)-borneol: efficacious positive modulators of GABA action at human recombinant α1β2γ2L GABAA receptors[J]. Biochemical pharmacology, 2005, 69(7): 1101-1111.

16. Cheng, C., Liu, X. W., Du, F. F., Li, M. J., Xu, F., Wang, F. Q., Sun, Y. Sensitive assay for measurement of volatile borneol, isoborneol, and the metabolite camphor in rat pharmacokinetic study of Borneolum (Bingpian) and Borneolum syntheticum (synthetic Bingpian)[J]. Acta Pharmacologica Sinica, 2013, 34(10): 1337.

17. Young, W. F., Horth, H., Crane, R., Ogden, T., Arnott, M. Taste and odour threshold concentrations of potential potable water contaminants[J]. Water Research, 1996, 30(2): 331-340.

18. Lv, C., Wu, X., Wang, X., Su, J., Zeng, H., Zhao, J., Zhang, W. The gene expression profiles in response to 102 traditional Chinese medicine (TCM) components: a general template for research on TCMs[J]. Scientific reports, 2017, 7(1): 352.