Nerolidol

Manufactured by Merck Group

Sourced in United States, Germany, China

Nerolidol is a naturally occurring sesquiterpene alcohol found in essential oils of various plants. It is a colorless liquid with a floral, woody aroma. Nerolidol functions as a chemical standard and analytical reference material for chemical and biological research.

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Lab products found in correlation

Geraniol, by Merck Group (7 mentions) Limonene, by Merck Group (6 mentions) Linalool, by Merck Group (5 mentions) Farnesol, by Merck Group (5 mentions) β pinene, by Merck Group (4 mentions) β caryophyllene, by Merck Group (4 mentions) Nerol, by Merck Group (4 mentions) Camphene, by Merck Group (3 mentions) β myrcene, by Merck Group (3 mentions) Eugenol, by Merck Group (3 mentions) Thymol, by Merck Group (3 mentions) P cymene, by Merck Group (3 mentions) Sabinene, by Merck Group (3 mentions) α pinene, by Merck Group (3 mentions) Geranyl acetate, by Merck Group (2 mentions) α bisabolol, by Merck Group (2 mentions) Caryophyllene oxide, by Merck Group (2 mentions) β farnesene, by Merck Group (2 mentions) α terpinene, by Merck Group (2 mentions) Benzaldehyde, by Merck Group (2 mentions)

Spelling variants of this product

Trans-nerolidol (8 citations) (E)-nerolidol (6 citations) Cis-nerolidol (5 citations) (Z)-nerolidol (2 citations)

28 protocols using nerolidol

Repellent Terpenoid Compounds Evaluation

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The molecules evaluated in this research were selected previously from Essential Oils (EOs) extracted from plants with potential repellent activity and tested by Centro de Investigaciones en Enfermedades Tropicales (CINTROP). The terpenoid compounds selected and with efficient repellent activity were the secondary metabolites: Geranyl acetate, α-bisabolol, and Nerolidol, purchased from Merck ©. The mentioned compounds have repellent activity confirmed and previously reported by CINTROP^{16 (link)}. The synthetic repellent DEET was used as a positive control (Fig. 1). All chemical reagents used in this work were purchased from Merck ©, USA.Figure 1

Molecules with repellent activity implemented in the electroantennography and proteomic assays (a) Geranyl acetate, (b) Nerolidol, (c) α-bisabolol, (d) DEET.

Portilla Pulido J.S., Urbina Duitama D.L., Velasquez-Martinez M.C., Mendez-Sanchez S.C, & Duque J.E. (2022). Differentiation of action mechanisms between natural and synthetic repellents through neuronal electroantennogram and proteomic in Aedes aegypti (Diptera: Culicidae). Scientific Reports, 12, 20397.

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Comprehensive Phytochemical Profiling of Extracts

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All the chemicals and reagents involved in the extraction processes, total polyphenolic content, antioxidant activity experiments and the chemical standards (1-hexanol, 2-Thujene, 3-octanone, 5-Amino-1-ethylprazole, Allylbenzene, Camphene, Caryophyllene oxide, Decanoic acid, Docosane, Germacrene D, Hexadecane, HexaDecanoic acid, Lavandulol, Limonene, Linalool, Linalool acetate, Nerol, Nerolidol, Ninanal, TetraDecanoic acid, Tricosane, α-Copaene, α-Humulene, α-Ter-pinene, β-Bourbonene, β-Caryophyllene, β-Copaene, β-Cubenene, β-Farnesene, β-Gurjunene, β-Myrcene, β-Pinene) used in the identification of phenolic and aromatic compounds from the extracts were acquired from Sigma Aldrich Company (St. Louis, MO, USA).

Stegăruș D.I., Lengyel E., Apostolescu G.F., Botoran O.R, & Tanase C. (2021). Phytochemical Analysis and Biological Activity of Three Stachys Species (Lamiaceae) from Romania. Plants, 10(12), 2710.

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Biochemical Compound Acquisition Protocol

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4-Hydroxy-2,5-dimethylfuran-3(2H)-one (HDMF), 2 (or 5)-ethyl-4-hydroxy-5 (or 2)-methylfuran-3(2H)-one (EHMF), 4-hydroxy-5-methylfuran-3(2H)-one (HMF), naringenin, eugenol, vanillic acid, salicylic acid, 1-naphthol, farnesol, sorbic acid, nerolidol, geraniol, fisetin, vanillin, chlorogenic acid, 2-naphthol, caffeic acid, methyl salicylate, ferulic acid, 1-octanol, and myricetin were purchased from Sigma-Aldrich (Shanghai, China). UDP-glucose, UDP-galactose, and UDP-glucuronic acid were purchased from Promega (Madison, USA). UDP-Xylose was purchased from Angfei Biotech Co., Ltd. (Guangzhou, China).

Chen Y., Guo X., Gao T., Zhang N., Wan X., Schwab W, & Song C. (2020). UGT74AF3 enzymes specifically catalyze the glucosylation of 4-hydroxy-2,5-dimethylfuran-3(2H)-one, an important volatile compound in Camellia sinensis. Horticulture Research, 7, 25.

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Insecticide Synergist Extraction Protocol

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Methomyl (purity 98%) was obtained from Jiangsu Jinghong Chemical Co. Ltd. (Yancheng, China). Piperonyl butoxide (PBO, purity 98%) was purchased from Nanchang Yangpu Natural Essence and Spice Co. Ltd. (Nanchang, China). Limonene, nerolidol, 2-heptanone, cis-3-hexenyl acetate, NADPH, glycerol, 7-ethoxycoumarin (7-EC), 7-hydroxycoumarin (7-HC), phenylmethylsulfonyl (PMSF), dithiothreitol (DTT), phenylthiourea (PTU) and bovine serum albumin (BSA) were obtained from Sigma (St. Louis, MO, USA). Acetone was purchased from Shanghai Ling Feng Chemical Reagent Co. Ltd. (Shanghai, China).

Wu C., Ding C., Chen S., Wu X., Zhang L., Song Y., Li W, & Zeng R. (2021). Exposure of Helicoverpa armigera Larvae to Plant Volatile Organic Compounds Induces Cytochrome P450 Monooxygenases and Enhances Larval Tolerance to the Insecticide Methomyl. Insects, 12(3), 238.

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Comprehensive Analysis of Volatile Compounds

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The standards of volatile compounds were purchased from Sigma-Aldrich (St. Louis, MO, USA), including isobutanol, 3-methyl-1-butanol, cis-3-hexen-1-ol, 1-hexanol, heptanol, octanol, phenethyl alcohol, 2,6-nonadien-1-ol, dodecanol, ethyl acetate, isoamyl acetate, ethyl lactate, ethyl hexanoate, ethyl octanoate, diethyl succinate, phenethyl acetate, ethyl decanoate, butanoic acid, hexanoic acid, octanoic acid, dodecanoic acid, octanal, (2e,6z)-2,6-nonadienal, benzaldehyde, furfural, citronellol, linalool, rose oxide, geraniol, nerol, β-damascenone, β-ionone, nerolidol, hexanal, guaiacol, 4-Ethylphenol, and 2-octanol which were used as the internal standard.
Folin–Ciocalteu reagent and sodium chloride were purchased from Beijing Chemical Works (Beijing, China). Potassium hydrogen tartrate were purchased at Kemiou Chemical Reagent Co. (Tianjin, China). Bovine serum albumin was obtained from Asahi Kasei Corporation (Tokyo, Japan). Deionized water (<18 MW resistance) was purified by using a Milli-Q purification system (Molecular, Chongqing, China). Bentonite, soybean protein and potassium metabisulfite were purchased from Lallemand Company (Lallemand, Toulouse, France).

Ma T.Z., Gong P.F., Lu R.R., Zhang B., Morata A, & Han S.Y. (2020). Effect of Different Clarification Treatments on the Volatile Composition and Aromatic Attributes of ‘Italian Riesling’ Icewine. Molecules, 25(11), 2657.

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Nerolidol and Doxorubicin Biochemical Assay

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The test compound, Nerolidol was purchased from Sigma Aldrich, St. Louis, MO, USA. Doxorubicin was purchased from EBEWE Pharma, Unterach, Mondseestrasse, Austria. The commercially available kits for the biochemical estimations were obtained from Sigma Aldrich, St. Louis, MO, USA and Abcam, MA, USA.

Arunachalam S., Nagoor Meeran M.F., Azimullah S., Sharma C., Goyal S.N, & Ojha S. (2021). Nerolidol Attenuates Oxidative Stress, Inflammation, and Apoptosis by Modulating Nrf2/MAPK Signaling Pathways in Doxorubicin-Induced Acute Cardiotoxicity in Rats. Antioxidants, 10(6), 984.

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Purchasing Volatile Compounds for Analysis

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Dihydrojasmone, p-cymene, carvacrol, thymol, farnesol and nerolidol were purchased from Sigma-Aldrich (St. Louis, MO, USA).

Serdeiro M.T., Dias T.D., de Lima N.T., Barbosa-Filho J.M., Belato R.D., dos Santos-Mallet J.R, & Maleck M. (2023). Study on Morphological Changes and Interference in the Development of Aedes aegypti Caused by Some Essential Oil Constituents. Tropical Medicine and Infectious Disease, 8(9), 440.

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Optimizing Nerolidol Formulations with Cyclodextrins

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Nerolidol (98%, mixture of cis (40%) and trans (60%) isomers), trans-Nerolidol (≥85%, analytical standard) and thymol (>99%) were purchased from Sigma-Aldrich (Missouri, United States). Cabreuva (Myrocarpus fastigiatus) essential oil (64.54% of trans-Ner) was purchased from Herbes et Traditions (Comines, France). Methylorange (MO) was provided by Acros Organics (Massachusetts, United States). α-CD, β-CD, HP-β-CD (DS = 5.6) and RAMEB (DS = 12.6) were purchased from Wacker-Chemie (Lyon, France). CRYSMEB (DS = 4.9) was provided from Roquette Frères (Lestrem, France). SBE-β-CD (DS = 6.5, Captisol^®) was donated by Ligand Pharmaceuticals Incorporated (La Jolla, USA). Methanol HPLC-grade was purchased from VWR Chemicals (Atlanta, United States).

Azzi J., Danjou P.E., Landy D., Ruellan S., Auezova L., Greige-Gerges H, & Fourmentin S. (2017). The effect of cyclodextrin complexation on the solubility and photostability of nerolidol as pure compound and as main constituent of cabreuva essential oil. Beilstein Journal of Organic Chemistry, 13, 835-844.

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Volatile Compounds Extraction Protocol

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2,3-Butanedione, 3-methyl-3-buten-2-one, 2-methyl-2-butanol, myrcene, α-phellandrene, 3-methyl-3-buten-1-ol, p-cymene, octanal, 1-octen-3-one, 6-methyl-5-heptene-2-one, (Z)-rose oxide, dimethyl trisulfide, (E)-2-octenal, methional, linalool, (E,Z)-2,6-nonadienal, isovaleric acid, (E,E)-2,4-nonadienal, citronellol, nerol, geraniol, guaiacol, nerolidol, 4-hydroxy-2,5-dimethyl-3(2H)-furanone (furaneol) and 2-ethyl-4-hydroxy-5-methyl-3(2H)-furanone (homofuraneol) were purchased from Sigma–Aldrich Chemicals Co. (St. Louis, MO). A mixture of n-alkanes (C7–C30) was used for the retention index (RI) analyses and was purchased from Sigma–Aldrich Chemicals Co. The extraction solvent, dichloromethane, was also purchased from Sigma–Aldrich Chemicals Co. and freshly distilled before use. Hexane was purchased from EMD Millipore Corporation (Darmstadt, Germany). Anhydrous sodium sulfate and sodium chloride were purchased from Fisher Scientific Co. (Hampton, NH).

Feng S., Huang M., Crane J.H, & Wang Y. (2017). Characterization of key aroma-active compounds in lychee (Litchi chinensis Sonn.). Journal of Food and Drug Analysis, 26(2), 497-503.

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Analytical Reagents for Phytochemical Analysis

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The following chemicals and reagents were used for the analyses: methanol (99.95%), acetonitrile (99.99%), and ammonium acetate, purchased from Carl Roth GmbH and Co. KG (Germany); tetrahydrofuran (99.7%) from VWR International GmbH (Germany); methyl tert-butyl ether (99.8%) from Geyer GmbH & Co. KG (Germany); formic acid (98-100%), dichloromethane (99.9%), isopropanol (99.95%), Tween 20 from Serva Electrophoresis GmbH (Germany); methyl salicylate (MeSA) and methyl jasmonate (MeJA) from Merck AG (Germany); C7-C40 alkanes (Supelco-49452-U), terpinenes (α, δ, ɣ), trans-β-ocimene, n-hexanal, nonanal, nerolidol, β-pinene, myrcene, sabinene, phellandrenes (α, β), β-caryophyllene and β-carotene from Sigma-Aldrich Chemie GmbH (Germany); α-carotene, (9Z)-neoxanthin, zeaxanthin, violaxanthin from CaroteNature GmbH (Switzerland). Lutein was isolated from Tagetes erecta by flash chromatography. After saponification, the lutein was purified and crystallized. Its structure was elucidated by NMR and high-resolution mass spectrometry (Baldermann, 2008 ), and compared to the authentic reference compound purchased from Sigma-Aldrich Chemie GmbH (Germany).

Errard A., Ulrichs C., Kühne S., Mewis I., Mishig N., Maul R., Drungowski M., Parolin P., Schreiner M, & Baldermann S. (2016). Metabolite Profiling Reveals a Specific Response in Tomato to Predaceous Chrysoperla carnea Larvae and Herbivore(s)-Predator Interactions with the Generalist Pests Tetranychus urticae and Myzus persicae. Frontiers in Plant Science, 7, 1256.

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