Geraniol — A review of a commercially important fragrance material

Abe, 2003, Suppression of tumor necrosis factor-alpha-induced neutrophil adherence responses by essential oils, Mediators of Inflammation, 12, 323, 10.1080/09629350310001633342

Aqil, 2007, Status of terpenes as skin penetration enhancers, Drug Discovery Today, 12, 1061, 10.1016/j.drudis.2007.09.001

Arellano, 1996, Enhancing effect of terpenes on the in vitro percutaneous absorption of diclofenac sodium, International Journal of Pharmaceutics, 130, 141, 10.1016/0378-5173(95)04364-0

Azarmi, 2009, Role of endothelium on relaxant effect of geraniol in isolated rat aorta, Pharmaceutical Science Winter, 14, 311

Bard, 1988, Geraniol interferes with membrane functions in strains of Candida and Saccharomyces, Lipids, 23, 534, 10.1007/BF02535593

Barnard, 2004, Laboratory evaluation of mosquito repellents against Aedes albopictus, Culex nigripalpus, and Ochlerotatus triseriatus (Diptera: Culicidae), Journal of Medical Entomology, 41, 726, 10.1603/0022-2585-41.4.726

Barros, 2009, In vitro larvicidal activity of geraniol and citronellal against Contracaecum sp (Nematoda: Anisakidae), Brazilian Journal of Medical and Biological Research, 42, 918, 10.1590/S0100-879X2009005000023

Başer, 2005, Ninde oil (Aeollanthus myrianthus Taylor) revisited: analysis of a historical oil, Journal of Essential Oil Research, 17, 137, 10.1080/10412905.2005.9698856

Baydar, 2005, The effects of harvest date, fermentation duration and Tween 20 treatment on essential oil content and composition of industrial oil rose (Rosa damascena Mill.), Industrial Crops and Products, 21, 251, 10.1016/j.indcrop.2004.04.004

Bedoukian, 1986, Geraniol and Nerol, 173

Bohlmann, 1998, Plant terpenoid synthase: molecular biology and phylogenetic analysis, Proceedings of National Academy of Sciences USA, 95, 4126, 10.1073/pnas.95.8.4126

Buckley, 2007, Fragrance ingredient labeling in products on sale in the UK, British Journal of Dermatology, 157, 295, 10.1111/j.1365-2133.2007.08018.x

Burdock, 2010, Geranio, 733

Burke, 1997, Inhibition of pancreatic cancer growth by the dietary isoprenoids farnesol and geraniol, Lipids, 32, 151, 10.1007/s11745-997-0019-y

Burke, 2002, Effects of the isoprenoids perillyl alcohol and farnesol on apoptosis biomarkers in pancreatic cancer chemoprevention, Anticancer Research, 22, 3127

Cantrell, 2001, Antimycobacterial plant terpenoids, Planta Medica, 67, 685, 10.1055/s-2001-18365

Cardullo, 1989, Allergic contact dermatitis resulting from sensitivity to citrus peel, geraniol, and citral, Journal of the American Academy Dermatology, 21, 395, 10.1016/S0190-9622(89)80043-X

Carnesecchi, 2001, Geraniol, a component of plant essential oils, inhibits growth and polyamine biosynthesis in human colon cancer cells, Journal of Pharmacology and Experimental Therapeutics, 298, 197

Carnesecchi, 2002, Geraniol, a component of plant essential oils, sensitizes human colonic cancer cells to 5-fluorouracil treatment, Journal of Pharmacology and Experimental Therapeutics, 301, 625, 10.1124/jpet.301.2.625

Carnesecchi, 2002, Perturbation by geraniol of cell membrane permeability and signal transduction pathways in human colon cancer cells, Journal of Pharmacology and Experimental Therapeutics, 302, 711, 10.1124/jpet.102.039263

Carnesecchi, 2004, Geraniol, a component of plant essential oils, modulates DNA synthesis and potentiates 5-fluorouracil efficacy on human colon tumor xenografts, Cancer Letters, 215, 53, 10.1016/j.canlet.2004.06.019

Choi, 2000, Radical-scavenging activities of citrus essential oils and their components: detection using 1, 1-diphenyl-2-picrylhydrazyl, Journal of Agriculture and Food Chemistry, 48, 4156, 10.1021/jf000227d

Clark, 1998, Geraniol, Perfumer & Flavorist, 23, 19

Dalleau, 2008, In vitro activity of terpenes against Candida biofilms, International Journal of Antimicrobial Agents, 31, 572, 10.1016/j.ijantimicag.2008.01.028

Demyttenaere, 1996, Biotransformation of geraniol and nerol by spores of Penicillium italicum, Phytochemistry, 41, 1079, 10.1016/0031-9422(95)00797-0

Demyttenaere, 2000, Biotransformation of geraniol, nerol and citral by sporulated surface cultures of Aspergillus niger and Penicillium sp, Phytochemistry, 55, 363, 10.1016/S0031-9422(00)00330-7

Doan, 2010, In vivo and in vitro skin absorption of lipophilic compounds, dibutyl phthalate, farnesol and geraniol in the hairless guinea pig, Food and Chemical Toxicology, 48, 18, 10.1016/j.fct.2009.09.002

Dubey, 2001, Biotransformation of geranyl acetate to geraniol during palmarosa (Cymbopogon martinii, Roxb. wats. var. motia) inflorescence development, Phytochemistry, 57, 675, 10.1016/S0031-9422(01)00122-4

Duncan, 2004, Geraniol and β-ionone inhibit proliferation, cell cycle progression, and cyclin-dependent kinase 2 activity in MCF-7 breast cancer cells independent of effects on HMG-CoA reductase activity, Biochemical Pharmacology, 68, 1739, 10.1016/j.bcp.2004.06.022

Edris, 2007, Pharmaceutical and therapeutic potentials of essential oils and their individual volatile constituents: a review, Phytotherapy Research, 21, 308, 10.1002/ptr.2072

Faria, 2009, Biotransformation of menthol and geraniol by hairy root cultures of Anethum graveolens: effect on growth and volatile components, Biotechnology Letters, 31, 897, 10.1007/s10529-009-9934-3

Friedman, 2002, Bactericidal activities of plant essential oils and some of their isolated constituents against Campylobacter jejuni, Escherichia coli, Listeriamonocytogenes, and Salmonella enterica, Journal of Food Protection, 10, 1545, 10.4315/0362-028X-65.10.1545

Ganjewala, 2009, Geranyl acetate esterase controls and regulates the level of geraniol in lemongrass (Cymbopogon flexuosus nees ex steud.) mutant cv. GRL-1 leaves, Zeitschrift für Naturforschung, 64c, 251, 10.1515/znc-2009-3-417

Garcia Moruno, 2002, Study of five strains of Saccharomyces cerevisiae with regard to their metabolism towards geraniol, International Journal of Vine and Wine Sciences, 36, 221

Godwin, 1999, Influence of drug lipophilicity on terpenes as penetration enhancers, Drug Development and Industrial Pharmacy, 25, 905, 10.1081/DDC-100102251

Goldstein, 1990, Regulation of the mevalonate pathway, Nature, 343, 425, 10.1038/343425a0

Gramatica, 1982, Stereospecific reduction of geraniol to (R)-(+)-citronellol by Saccharomyces cerevisiae, Cellular and Molecular Life Sciences, 38, 775, 10.1007/BF01972264

Greif, 1967, Cutaneous safety of fragrance materials as measured by the maximization test, American Perfumer and Cosmetics, 82, 54

Hagan, 1967, Food flavourings and compounds of related structure: subacute and chronic toxicity, Food and Cosmetics Toxicology, 5, 141, 10.1016/S0015-6264(67)82961-4

Hagvall, 2007, Fragrance compound geraniol forms contact allergens on air exposure. Identification and quantification of oxidation products and effect on skin sensitization, Chemical Research in Toxicology, 20, 807, 10.1021/tx700017v

Hagvall, 2008, Cytochrome P450-mediated activation of the fragrance compound geraniol forms potent contact allergens, Toxicology and Applied Pharmacology, 233, 308, 10.1016/j.taap.2008.08.014

Hanif, 1998, Penetration enhancing effect of tetrahydrogeraniol on the percutaneous absorption of 5-fluorouracil from gels in excised rat skin, Journal of Control Release, 55, 297, 10.1016/S0168-3659(98)00062-5

Hao, 2008, Host-seeking and blood-feeding behavior of Aedes albopictus (Diptera: Culicidae) exposed to vapors of geraniol, citral, citronellal, eugenol, or anisaldehyde, Journal of Medical Entomology, 45, 533, 10.1603/0022-2585(2008)45[533:HABBOA]2.0.CO;2

Hierro, 2006, In vivo larvicidal activity of monoterpenic derivatives from aromatic plants against L3 larvae of Anisakis simplex s.l, Phytomedicine, 13, 527, 10.1016/j.phymed.2005.05.001

Hierro, 2004, Action of different monoterpenic compounds against Anisakis simplex s.l. L3 larvae, Phytomedicine, 11, 77, 10.1078/0944-7113-00375

Howes, 2002, Assessment of estrogenic activity in some common essential oil constituents, Journal of Pharmacy and Pharmacology, 54, 1521, 10.1211/002235702216

Iijima, 2004, Characterization of geraniol synthase from the peltate glands of sweet basil, Plant Physiology, 134, 370, 10.1104/pp.103.032946

Inouye, 2001, Antibacterial activity of essential oils and their major constituents against respiratory tract pathogens by gaseous contact, Journal of Antimicrobial Chemotherapy, 47, 565, 10.1093/jac/47.5.565

Ishidate, 1984, Primary mutagenicity screening of food additives currently used in Japan, Food and Chemical Toxicology, 22, 623, 10.1016/0278-6915(84)90271-0

Jakobisiak, 2003, Potential antitumor effects of statins, International Journal of Oncology, 23, 1055

Jeon, 2009, Food protective effect of geraniol and its congeners against stored food mites, Journal of Food Protection, 72, 1468, 10.4315/0362-028X-72.7.1468

Ji, 2002, Monoterpene geraniol prevents acute allograft rejection, Transplantation Proceedings, 34, 1418, 10.1016/S0041-1345(02)02910-X

Khallaayoune, 2009, Efficacy of 1% geraniol (Fulltec) as a tick repellent, Parasite, 16, 223, 10.1051/parasite/2009163223

Kigasawa, 2009, In vivo transdermal delivery of diclofenac by ion-exchange iontophoresis with geraniol, Biological and Pharmaceutical Bulletin, 32, 684, 10.1248/bpb.32.684

Knobloch, 1989, Antibacterial and antifungal properties of essential oil components, Journal of Essential Oil Research, 1, 118, 10.1080/10412905.1989.9697767

Kumaran, 2003, Geraniol, the putative anthelmintic principle of Cymbopogon martinii, Phytotherapy Research, 17, 957, 10.1002/ptr.1267

Lapczynski, 2008, Fragrance material review on geraniol, Food and Chemical Toxicology, 46, S160, 10.1016/j.fct.2008.06.048

Leela, 1992, Nematicidal activity of essential oil of Pelargonium graveolens against the root-knot nematode Meloidogyne incognita, Nematologia Mediterranea, 20, 57

Lorenzi, 2009, Geraniol restores antibiotic activities against multidrug-resistant isolates from gram-negative species, Antimicrobial Agents and Chemotherapy, 53, 2209, 10.1128/AAC.00919-08

Luan, 2002, Differential incorporation of 1-deoxy-D-xylulose into (3S)-linalool and geraniol in grape berry exocarp and mesocarp, Phytochemistry, 60, 451, 10.1016/S0031-9422(02)00147-4

Luan, 2005, Metabolism of geraniol in grape berry mesocarp of Vitis vinifera L. cv. Scheurebe: demonstration of stereoselective reduction, E/Z-isomerization, oxidation and glycosylation, Phytochemistry, 66, 295, 10.1016/j.phytochem.2004.12.017

Mahmoud, 2002, Strategies for transgenic manipulation of monoterpene biosynthesis in plants, Trends in Plant Science, 7, 366, 10.1016/S1360-1385(02)02303-8

Mans, 1999, Sequence dependent growth inhibition and DNA damage formation by the irinotecan-5-fluorouracil combination in human colon carcinoma cell lines, European Journal of Cancer, 35, 1851, 10.1016/S0959-8049(99)00222-1

Maruyama, 2008, Protective activity of geranium oil and its component, geraniol, in combination with vaginal washing against vaginal candidiasis in mice, Biological and Pharmaceutical Bulletin, 31, 1501, 10.1248/bpb.31.1501

Moghimi, 2009, Enhancement effect of terpenes on silver sulphadiazine permeation through third-degree burn eschar, Burns, 35, 1165, 10.1016/j.burns.2009.02.006

Müller, 2008, Indoor protection against mosquito and sand fly bites: a comparison between citronella, linalool, and geraniol candles, Journal of the American Mosquito Control Association, 24, 150, 10.2987/8756-971X(2008)24[150:IPAMAS]2.0.CO;2

Müller, 2009, Efficacy of the botanical repellents geraniol, linalool, and citronella against mosquitoes, Journal of Vector Ecology, 2, 10.1111/j.1948-7134.2009.00002.x

Navarro, 2008, Anisakis simplex s.l.: larvicidal activity of various monoterpenic derivatives of natural origin against L3 larvae in vitro and in vivo, Experimental Parasitology, 120, 295, 10.1016/j.exppara.2008.07.014

Nokhodchi, 2007, The effect of terpene concentrations on the skin penetration of diclofenac sodium, International Journal of Pharmaceutics, 335, 97, 10.1016/j.ijpharm.2006.10.041

Nunes, 2009, Menthol and geraniol biotransformation and glycosylation capacity of Levisticum officinale hairy roots, Planta Medica, 75, 387, 10.1055/s-0028-1112217

Omolo, 2004, Repellency of essential oils of some Kenyan plants against Anopheles gambiae, Phytochemistry, 65, 2797, 10.1016/j.phytochem.2004.08.035

Ong, 2006, Farnesol and geraniol chemopreventive activities during the initial phases of hepatocarcinogenesis involve similar actions on cell proliferation and DNA damage, but distinct actions on apoptosis, plasma cholesterol and HMGCoA reductase, Carcinogenesis, 27, 1194, 10.1093/carcin/bgi291

Papachristos, 2004, The relationship between the chemical composition of three essential oils and their insecticidal activity against Acanthoscelides obtectus (Say), Pest Management Science, 60, 514, 10.1002/ps.798

Pattanayak, 2009, Geraniol and limonene interaction with 3-hydroxy-3-methylglutaryl CoA (HMG-CoA) reductase for their role as cancer chemo-preventive agents, Journal of Proteomics & Bioinformatics, 11, 466, 10.4172/jpb.1000107

Peffley, 2003, Plant-derived monoterpenes suppress hamster kidney cell 3-hydroxy-3-methylglutaryl coenzyme a reductase synthesis at post-transcriptional level, The Journal of Nutrition, 133, 38, 10.1093/jn/133.1.38

Polo, 2006, Effect of geraniol on fatty acid and mevalonate metabolism in the human hepatoma cell line Hep G2, Biochemistry and Cell Biology, 84, 102, 10.1139/o05-160

Prashar, 2003, Antimicrobial action of palmarosa oil (Cymbopogon martinii) on Saccharomyces cerevisiae, Phytochemistry, 63, 569, 10.1016/S0031-9422(03)00226-7

Price, 2006, Comparison of effects of octopamine and insecticidal essential oils on activity in the nerve cord, foregut, and dorsal unpaired median neurons of cockroaches, Journal of Insect Physiology, 52, 309, 10.1016/j.jinsphys.2005.11.010

Qualls, 2009, Field evaluation of three botanical repellents against Psorophora ferox, Aedes atlanticus, and Aedes mitchellae, Journal of the American Mosquito Control Association, 25, 379, 10.2987/09-5850.1

Rajeswara Rao, 2004, Yellowing and crinkling disease and its impact on the yield and composition of the essential oil of citronella (Cymbopogon winterianus Jowitt.), Flavour and Fragrance Journal, 19, 344, 10.1002/ffj.1313

Rama Devi, 1978, Molecular rearrangements in the microbiological transformations of terpenes and the chemical logic of microbial processes, Journal of the Indian Chemistry Society, 55, 1131

Rastogi, 1996, Natural ingredients based cosmetics. Content of selected fragrance sensitizers, Contact Dermatitis, 34, 423, 10.1111/j.1600-0536.1996.tb02246.x

Rastogi, 1998, Deodorants on the European market: quantitative chemical analysis of 21 fragrances, Contact Dermatitis, 38, 29, 10.1111/j.1600-0536.1998.tb05633.x

Rastogi, 2001, Fragrance chemicals in domestic and occupational products, Contact Dermatitis, 45, 221, 10.1034/j.1600-0536.2001.450406.x

Regev, 1976, Analyses of pharate female twospotted spider mites for nerolidol and geraniol: evaluation for sex attraction of males, Environmental Entomology, 5, 133, 10.1093/ee/5.1.133

Rosato, 2007, Antibacterial effect of some essential oils administered alone or in combination with Norfloxacin, Phytomedicine, 14, 727, 10.1016/j.phymed.2007.01.005

Sato, 2007, Antimicrobial effect of vapours of geraniol, (R)-(−)-linalool, terpineol, γ-terpinene and 1, 8-cineole on airbone microbes using an airwasher, Flavour and Fragrance Journal, 22, 435, 10.1002/ffj.1818

Scortichini, 2008, In vitro susceptibility of Erwinia amylovora (Burrill) Winslow et al. to geraniol and citronellol, Journal of Applied Microbiology, 71, 113

Seo, 2008, The monoterpenoids citral and geraniol are moderate inhibitors of CYP2B6 hydroxylase activity, Chemico-Biological Interactions, 174, 141, 10.1016/j.cbi.2008.06.003

Seubert, 1964, Untersuchungen über den bakteriellen Abbau von Isoprenoiden: V. Der Mechanismus des Isoprenoidabbaues, Biochemische Zeitschrift, 341, 35

Shin, 2004, Antifungal effects of herbal essential oils alone and in combination with ketoconazole against Trichophyton spp, Journal of Applied Microbiology, 97, 1289, 10.1111/j.1365-2672.2004.02417.x

Shoji, 1998, Enhancement of anti-herpetic activity of antisense phosphorothioate oligonucleotides 5′ end modified with geraniol, Journal of Drug Targeting, 5, 261, 10.3109/10611869808995880

Si, 2006, Antimicrobial activity of essential oils and structurally related synthetic food additives towards selected pathogenic and beneficial gut bacteria, Journal of Applied Microbiology, 100, 296, 10.1111/j.1365-2672.2005.02789.x

Simon, 1986, Extraction by hydrodiffusion of the essential oil of Monarda fistulosa grown in the province of Quebec: assay of geraniol in the hydrodiffused oil, Pharmaceutical Biology, 24, 120

Suppakul, 2003, Antimicrobial properties of basil and its possible application in food packaging, Journal of Agriculture and Food Chemistry, 51, 3197, 10.1021/jf021038t

Takechi, 2006, Biotransformation of geraniol by the larvae of common cutworm (Spodoptera litura), Journal of Oleo Science, 55, 143, 10.5650/jos.55.143

Thompson, 2010, Biotransformation of β-myrcene to geraniol by a strain of Rhodococcus erythropolis isolated by selective enrichment from hop plants, Applied Microbiology and Biotechnology, 85, 721, 10.1007/s00253-009-2182-6

Tiwari, 2009, Plant derived antioxidants-geraniol and camphene protect rat alveolar macrophages against t-BHP induced oxidative stress, Toxicology in Vitro, 23, 295, 10.1016/j.tiv.2008.12.014

Traina, 2005, In vitro acaricidal activity of four monoterpenes and solvents against Otodectes cynotis (Acari: Psoroptidae), Experimental and Applied Acarology, 37, 141, 10.1007/s10493-005-0359-y

Van Zyl, 2006, The biological activities of 20 nature identical essential oil constituents, The Journal of Essential Oil Research, 18, 129, 10.1080/10412905.2006.12067134

Viollon, 1994, Antifungal properties of essential oils and their main components upon Cryptococcus neoformans, Mycopathologia, 128, 151, 10.1007/BF01138476

Wiseman, 2007, Cell cycle arrest by the isoprenoids perilly alcohol, geraniol, and farnesol is mediated by p21Cip1 and p27Kip1 in human pancreatic adenocarcinoma cells, The Journal of Pharmacology and Experimental Therapeutics, 320, 1163, 10.1124/jpet.106.111666

Wolken, 2001, Geraniol biotransformation-pathway in spores of Penicillium digitatum, Applied Microbiology and Biotechnology, 57, 731, 10.1007/s002530100821

Wood, 1969, Microbial fermentation of lower terpenoids, Process Biochemistry, 2, 50

Yang, 2005, A geraniol-synthase gene from Cinnamomum tenuipilum, Phytochemistry, 66, 285, 10.1016/j.phytochem.2004.12.004

Yu, 1995, Geraniol, an inhibitor of mevalonate biosynthesis, suppresses the growth of hepatomas and melanomas transplanted to rats and mice, Journal of Nutrient, 125, 2763

Yu, 1995, Efficacy of beta-ionone in the chemoprevention of rat mammary carcinogenesis, Journal of Agriculture and Food Chemistry, 43, 2144, 10.1021/jf00056a035

Zhang, 2006, Antifungal activities of major tea leaf volatile constituents toward Colletorichum camelliae Massea, Journal of Agricultural and Food Chemistry, 54, 3936, 10.1021/jf060017m