2D Structure

3D Structure

Geraniol


Properties
PID PID00040
Mol. Weight 154.253 g/mol
LogP 3.56
Water solubility In water, 100 mg/L at 25 °C
Hydrogen Bond Donor 1
Hydrogen Bond Acceptor 1
Rotatable Bonds 4
XLogP3-AA 2.9

Geraniol

Identifiers
Formula C10H18O
PubChem CID 637566
FEMA 2507
Flavor Profile Geranium, Lemon Peel, Passion Fruit, Peach, Rose; Sweet Rose Odor, Pleasant Geranium-Like Odor, Pleasant, Floral Odor; Taste Threshold Values: Taste Characteristics At 10 Ppm; Sweet Floral Rose, Citrus With Fruity, Waxy Nuances
Smiles CC(C)=CCC/C(C)=C/CO
InChl Key GLZPCOQZEFWAFX-JXMROGBWSA-N
InChl InChI=1S/C10H18O/c1-9(2)5-4-6-10(3)7-8-11/h5,7,11H,4,6,8H2,1-3H3/b10-7+
CAS Registry Number 106-24-1, 624-15-7, 68311-14-8, 106-25-2
IUPAC Systematic Name (2E)-3,7-dimethylocta-2,6-dien-1-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
Fortune Eupatorium Equivalent plant: Eupatorium fPei Lan(佩兰)Eupatorii HerbaNeural, PungentLung,Spleen,StomachView Graph
Allium sativumDa Suan(大蒜)GarlicWarm,PungentSpleen, Stomach, Kidney, LungView Graph
Murraya paniculata [Syn. Chalcas paniculata]Jiu Li Xiang(九里香)Common Jasminorange Equivalent plant: Murraya panNeural, Bitter, PungentLungView Graph
Exocarpium Citri RubrumJu Hong (橘红)Citri Exocarpium RubrumWarm, Pungent, BitterSpleen, LiverView Graph
Medicinal IndianmulberryBa Ji Tian(巴戟天)Morindae Officinalis RadixWarm, Pungent, SweetLung, Bladder, HeartView Graph
TsaokoCao Guo (草果)Tsaoko FructusWarm, PungentLung, Spleen, StomachView 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
Eucommia ulmoidesDu Zhong Ye(杜仲叶)Eucommia LeafWarm,PungentSpleen, Stomach, Kidney, LungView 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
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
Exocarpium Citri RubrumJu Hong (橘红)Citri Exocarpium RubrumWarm, Pungent, BitterSpleen, LiverView Graph
Geranium wilfordiiLao Guan Cao(老鹳草)Wilford Cranesbill Equivalent plant: Erodium stepMild,Pungent,BitterSpleen,HeartView Graph
Chinese Ephedra Equivalent plant: Ephedra equisetiMa Huang (麻黄)Ephedrae HerbaWarm, Pungent, Slightly BitterLung, BladderView Graph
MyrrhMo Yao (没药)MyrrhaNeutral, Pungent, BitterSpleen, Liver, Heart, KidneyView Graph
rhizome of Obscured HomalomenaQian Nian Jian(千年健)Homalomenae RhizomaWarm, Bitter, PungentSpleen, Large Intestine, Stomach, Gallbladder, Three EndView Graph
Villous Amomum Equivalent plant: Amomum xanthioideSha Ren (砂仁)Amomi FructusWarm, PungentLung, Spleen, StomachView Graph
Fresh Common GingerSheng Jiang (生姜)Zingiber Rhizoma RecensWarm, PungentLung, Spleen, StomachView Graph
Wilson CitronXiang Yuan(香橼)Citri FructusWarm, Pungent, Sour, Slightly BitterLung, Spleen, LiverView Graph
Lily Magnolia Buds Equivalent plant: Magnolia liliXin Yi (辛夷)Magnoliae FlosWarm, PungentLung, Spleen, StomachView Graph

Pharmacological action

Geraniol (3,7-dimethyl-2,6-octadien-1-ol), an acyclic monoterpenealcohol with the chemical formula C10H18O, represents a new class of chemopreventive agents,

which is found in lemon, lemongrass, essential oils of fruits and herbs, and aromatic herb oil. It is considered as generally-recognized-as-safe (GRAS) by FDA.

Geraniol is an acyclic monoterpene alcohol commonly used as a flavoring agent.

Geraniol is the main ingredient in oil of rose and palmorosa and it is found as an active constituent in the essential oil of lemongrass, ginger, orange,

lavender, lime, citronella, nutmeg and other plants. It has been shown to exert antitumor and antioxidant activities against various cancer types. Geraniol

appears as a clear to pale-yellow oil which is insoluble in water, but soluble in most organic solvents.Geraniol has characteristic rose-like odour and the

taste (at 10 ppm) is described as sweet floral rose-like, citrus with fruity, waxy nuances.

Geraniol, a monoterpene extracted from plants, has been reported to be an effective antioxidant in arious metabolic disorders, attenuating atherosclerosis,

hyperlipidemia, oxidative stress, inflammation and fibrosis in multiple organs, and increased serum NO levels in hamsters reversing raised systolic blood

pressure (SBP), uric acid level and glucose associated index in rats with fructose induced metabolism syndrome.

Geraniol is a commercially important terpene alcohol occurring in the essential oils of several aromatic plants. Geraniol is known to exhibit insecticidal

and repellent properties and used as a natural pest control agent exhibiting low toxicity.



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 Madankumar A, Tamilarasi S, Premkumar T, et al. Geraniol attenuates 4NQO-induced tongue carcinogenesis through downregulating the activation of NF-κB in rats[J]. Molecular and cellular biochemistry, 2017, 434(1-2): 7-15.

2 Tsai M L, Lin C C, Lin W C, et al. Antimicrobial, antioxidant, and anti-inflammatory activities of essential oils from five selected herbs[J]. Bioscience, biotechnology, and biochemistry, 2011, 75(10): 1977-1983.

3 Madankumar A, Jayakumar S, Devaki T. Geraniol, a component of plant essential oils prevents experimental oral carcinogenesis by modulating glycoprotein abnormalities and membrane bound atpase’s[J]. Int J Pharm Pharm Sci, 2013, 5(1): 416.

4 Vinothkumar V, Manoharan S, Sindhu G, et al. Geraniol modulates cell proliferation, apoptosis, inflammation, and angiogenesis during 7, 12-dimethylbenz [a] anthracene-induced hamster buccal pouch carcinogenesis[J]. Molecular and cellular biochemistry, 2012, 369(1-2): 17-25.

5 Ahmad S T, Arjumand W, Seth A, et al. Preclinical renal cancer chemopreventive efficacy of geraniol by modulation of multiple molecular pathways[J]. Toxicology, 2011, 290(1): 69-81.

6 Madankumar A, Jayakumar S, Gokuladhas K, et al. Geraniol modulates tongue and hepatic phase I and phase II conjugation activities and may contribute directly to the chemopreventive activity against experimental oral carcinogenesis[J]. European journal of pharmacology, 2013, 705(1-3): 148-155.

7 Madankumar A, Jayakumar S, Asokkumar S, et al. Chemopreventive potential of geraniol on 4-Nitroquinoline-1 oxide induced oral carcinogenesis in rats[J]. Int. J. Res. Pharm. Sci, 2011, 2: 531-536.

8 Deepak V, Kruger M C, Coetzee M. Geraniol attenuates osteoclast differentiation by suppressingNF-kB activity and expression of osteoclastogenic genes[J]. Medicinal Chemistry Research, 2017, 26(1): 19-26.

9 Medicherla K, Sahu B D, Kuncha M, et al. Oral administration of geraniol ameliorates acute experimental murine colitis by inhibiting pro-inflammatory cytokines and NF-κB signaling[J]. Food & function, 2015, 6(9): 2984-2995.

10 Chen W, Viljoen A M. Geraniol—a review of a commercially important fragrance material[J]. South African Journal of Botany, 2010, 76(4): 643-651.

11 Burdock, G.A., 2010. Geranio, Fenaroli's Handbook of Flavor Ingredients, 6thed. CRC Press, pp. 733–734.

12 Burke Y D, Stark M J, Roach S L, et al. Inhibition of pancreatic cancer growth by the dietary isoprenoids farnesol and geraniol[J]. Lipids, 1997, 32(2): 151.

13 Yu S G, Hildebrandt L A, Elson C E. Geraniol, an inhibitor of mevalonate biosynthesis, suppresses the growth of hepatomas and melanomas transplanted to rats and mice[J]. The Journal of nutrition, 1995, 125(11): 2763-2767.

14 Sato K, Krist S, Buchbauer G. Antimicrobial effect of vapours of geraniol,(R)‐(–)‐linalool, terpineol, γ‐terpinene and 1, 8‐cineole on airborne microbes using an airwasher[J]. Flavour and Fragrance Journal, 2007, 22(5): 435-437.

15 Barnard D R, Xue R D. Laboratory evaluation of mosquito repellents against Aedes albopictus, Culex nigripalpus, and Ochlerotatus triseriatus (Diptera: Culicidae)[J]. Journal of medical entomology, 2004, 41(4): 726-730.

16 Wang X, Zhao S, Su M, et al. Geraniol improves endothelial function by inhibiting NOX-2 derived oxidative stress in high fat diet fed mice[J]. Biochemical and biophysical research communications, 2016, 474(1): 182-187.

17 Jayachandran M, Chandrasekaran B, Namasivayam N. Geraniol attenuates oxidative stress by Nrf2 activation in diet-induced experimental atherosclerosis[J]. Journal of basic and clinical physiology and pharmacology, 2015, 26(4): 335-346.

18 Jayachandran M, Chandrasekaran B, Namasivayam N. Effect of geraniol, a plant derived monoterpene on lipids and lipid metabolizing enzymes in experimental hyperlipidemic hamsters[J]. Molecular and cellular biochemistry, 2015, 398(1-2): 39-53.

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

20 Chen J, Fan X, Zhou L, et al. Treatment with geraniol ameliorates methionine‐choline‐deficient diet‐induced non‐alcoholic steatohepatitis in rats[J]. Journal of gastroenterology and hepatology, 2016, 31(7): 1357-1365.

21 Jayachandran M, Chandrasekaran B, Namasivayam N. Geraniol attenuates fibrosis and exerts anti-inflammatory effects on diet induced atherogenesis by NF-κB signaling pathway[J]. European journal of pharmacology, 2015, 762: 102-111.

22 Kim S H, Bae H C, Park E J, et al. Geraniol inhibits prostate cancer growth by targeting cell cycle and apoptosis pathways[J]. Biochemical and Biophysical Research Communications, 2011, 407(1): 129-134.

23 Prasad S N. Neuroprotective effect of geraniol and curcumin in an acrylamide model of neurotoxicity in Drosophila melanogaster: relevance to neuropathy[J]. Journal of insect physiology, 2014, 60: 7-16.

24 Rekha K R, Selvakumar G P, Sethupathy S, et al. Geraniol ameliorates the motor behavior and neurotrophic factors inadequacy in MPTP-induced mice model of Parkinson’s disease[J]. Journal of Molecular Neuroscience, 2013, 51(3): 851-862.

25 de Carvalho K I M, Bonamin F, dos Santos R C, et al. Geraniol—a flavoring agent with multifunctional effects in protecting the gastric and duodenal mucosa[J]. Naunyn-Schmiedeberg's archives of pharmacology, 2014, 387(4): 355-365.

26 Carnesecchi S, Bras-Gonçalves R, Bradaia A, et al. Geraniol, a component of plant essential oils, modulates DNA synthesis and potentiates 5-fluorouracil efficacy on human colon tumor xenografts[J]. Cancer Letters, 2004, 215(1): 53-59.

27 Crowell P L. Prevention and therapy of cancer by dietary monoterpenes[J]. The Journal of nutrition, 1999, 129(3): 775S-778S.

28 Tiwari M, Kakkar P. Plant derived antioxidants–geraniol and camphene protect rat alveolar macrophages against t-BHP induced oxidative stress[J]. Toxicology in vitro, 2009, 23(2): 295-301.

29 Cardozo M T, de Conti A, Ong T P, et al. Chemopreventive effects of β-ionone and geraniol during rat hepatocarcinogenesis promotion: distinct actions on cell proliferation, apoptosis, HMGCoA reductase, and RhoA[J]. The Journal of nutritional biochemistry, 2011, 22(2): 130-135.

30 de March C A, Ryu S E, Sicard G, et al. Structure–odour relationships reviewed in the postgenomic era[J]. Flavour and fragrance journal, 2015, 30(5): 342-361.

31 Knape K, Beyer A, Stary A, et al. Evolutionary trace of human odorant receptors of chromosome 17[J]. Flavour and fragrance journal, 2009, 24(4): 192-197.

32 Oh E H, Lee S H, Lee S H, et al. Cell-based high-throughput odorant screening system through visualization on a microwell array[J]. Biosensors and Bioelectronics, 2014, 53: 18-25.

33 Katsukawa M, Nakata R, Koeji S, et al. Citronellol and geraniol, components of rose oil, activate peroxisome proliferator-activated receptor α and γ and suppress cyclooxygenase-2 expression[J]. Bioscience, biotechnology, and biochemistry, 2011, 75(5): 1010-1012.

34 Ali I, Satti N K, Dutt P, et al. Hydroxychavicol: A phytochemical targeting cutaneous fungal infections[J]. Scientific reports, 2016, 6: 37867.

35 Impaired odour discrimination on desynchronization of odour-encoding neural assemblies

36 Denby C M, Li R A, Vu V T, et al. Industrial brewing yeast engineered for the production of primary flavor determinants in hopped beer[J]. Nature communications, 2018, 9(1): 965.

37 Gire D H, Whitesell J D, Doucette W, et al. Information for decision-making and stimulus identification is multiplexed in sensory cortex[J]. Nature neuroscience, 2013, 16(8): 991.

38 Singh S, Fatima Z, Hameed S. Insights into the mode of action of anticandidal herbal monoterpenoid geraniol reveal disruption of multiple MDR mechanisms and virulence attributes in Candida albicans[J]. Archives of microbiology, 2016, 198(5): 459-472.

39 Gruntman E, Turner G C. Integration of the olfactory code across dendritic claws of single mushroom body neurons[J]. Nature neuroscience, 2013, 16(12): 1821.

40 Kermen F, Chakirian A, Sezille C, et al. Molecular complexity determines the number of olfactory notes and the pleasantness of smells[J]. Scientific reports, 2011, 1: 206.

41 Uchida N, Takahashi Y K, Tanifuji M, et al. Odor maps in the mammalian olfactory bulb: domain organization and odorant structural features[J]. Nature neuroscience, 2000, 3(10): 1035.

42 Cao L H, Yang D, Wu W, et al. Odor-evoked inhibition of olfactory sensory neurons drives olfactory perception in Drosophila[J]. Nature communications, 2017, 8(1): 1357.

43 Moberg P J, Agrin R, Gur R E, et al. Olfactory dysfunction in schizophrenia: a qualitative and quantitative review[J]. Neuropsychopharmacology, 1999, 21(3): 325-340.

44 Perez-Orive J, Mazor O, Turner G C, et al. Oscillations and sparsening of odor representations in the mushroom body[J]. Science, 2002, 297(5580): 359-365.

45 Segade S R, Vilanova M, Giacosa S, et al. Ozone improves the aromatic fingerprint of white grapes[J]. Scientific reports, 2017, 7(1): 16301.

46 Ito I, Ong R C, Raman B, et al. Sparse odor representation and olfactory learning[J]. Nature neuroscience, 2008, 11(10): 1177.

47 Davidovich-Rikanati R, Sitrit Y, Tadmor Y, et al. Enrichment of tomato flavor by diversion of the early plastidial terpenoid pathway[J]. Nature biotechnology, 2007, 25(8): 899.

48 Kim K S, Lee I S, Kim K H, et al. Activation of intestinal olfactory receptor stimulates glucagon-like peptide-1 secretion in enteroendocrine cells and attenuates hyperglycemia in type 2 diabetic mice[J]. Scientific Reports, 2017, 7(1): 13978.

49 Hernandez-Ortega A, Vinaixa M, Zebec Z, et al. A toolbox for diverse oxyfunctionalisation of monoterpenes[J]. Scientific reports, 2018, 8.

50 Saha D, Leong K, Li C, et al. A spatiotemporal coding mechanism for background-invariant odor recognition[J]. Nature neuroscience, 2013, 16(12): 1830.

51 Nizampatnam S, Saha D, Chandak R, et al. Dynamic contrast enhancement and flexible odor codes[J]. Nature communications, 2018, 9(1): 3062.

52 Galizia C G, Sachse S, Rappert A, et al. The glomerular code for odor representation is species specific in the honeybee Apis mellifera[J]. Nature neuroscience, 1999, 2(5): 473.

53 Vincis R, Gschwend O, Bhaukaurally K, et al. Dense representation of natural odorants in the mouse olfactory bulb[J]. Nature neuroscience, 2012, 15(4): 537.

54 Kermen F, Midroit M, Kuczewski N, et al. Topographical representation of odor hedonics in the olfactory bulb[J]. Nature neuroscience, 2016, 19(7): 876.

55 Ohtawa M, Arima S, Shimizu R, et al. Development of a new air-stable structure-simplified nafuredin-γ analog as a potent and selective nematode complex I inhibitor[J]. The Journal of antibiotics, 2017, 70(5): 647.

56 https://en.wikipedia.org/wiki/Geraniol