This compound belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle.
External Descriptors
Acyclic monoterpenoids
1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.
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Application Protocols
No immunoassay or bioassay application protocols (e.g., WB, IHC, IF, FC) are applicable to this small-molecule reagent. For synthetic or analytical uses, follow reaction-specific procedures under Reaction Conditions and Synthetic Utility. For GC/LC method development, establish instrument parameters empirically (e.g., nonpolar GC column, temperature ramp suitable for bp ~225–230 °C; or RP-LC with C18 and high-organic mobile phase).
Biological Roles
General biochemistry (literature; not product-specific)
Nerol is a plant metabolite found in numerous essential oils (e.g., neroli, lemongrass, hops). It arises from the isoprenoid biosynthetic pathway (IPP/DMAPP → geranyl pyrophosphate → monoterpene alcohols), representing the cis-geometry isomer of geraniol.
Functions in plants may include roles in aroma-mediated ecological interactions (pollinator attraction, herbivore deterrence) and as a precursor to glycosidically bound terpenes.
Metabolic fate (literature)
In biological systems, primary oxidation can yield the corresponding aldehyde (neral) and ultimately acids; conjugation (e.g., glucuronidation, sulfation) enhances excretion in mammals.
Enzymatic transformations include alcohol dehydrogenases, cytochrome P450-mediated epoxidation/hydroxylation, and terpene synthase-catalyzed rearrangements.
Laboratory relevance
Used as a model substrate in studies of allylic alcohol oxidation, mono-/dioxygenase activity, and isomerization catalysis due to its defined E/Z alkene geometry.
Note
The above roles are literature context for nerol and do not imply any medical or therapeutic application. This product is for research use only.
Buffer Applications
Nerol is a hydrophobic monoterpenoid alcohol and is not a buffering agent. It has no defined acid/base pair in the physiological pH range.
Practical note
For experiments requiring aqueous buffers containing nerol (e.g., biotransformations), dissolve nerol first in a small volume of a miscible co-solvent (ethanol, DMSO, or Tween-containing micelles) before addition to the buffer to ensure homogeneity.
Choose buffer based on the biological system (e.g., phosphate, Tris, HEPES); nerol does not contribute to buffering capacity.
Green Alternatives
Although nerol is not primarily used as a solvent, its sourcing and use have green chemistry implications.
Bio-based origin (general)
Nerol is a plant-derived monoterpene alcohol (commonly from essential oils), aligning with renewable feedstock principles when sourced sustainably.
Comparing carriers/solvents for work with nerol (literature-based guidance)
| Option | Origin | Boiling point | Pros | Cons |
|---|---|---|---|---|
| Ethanol (bio-ethanol) | Renewable | 78 °C | Low toxicity, biodegradable, widely accepted | Polar; may not dissolve very hydrophobic matrices |
| 2-MeTHF | Often bio-based (furfural) | 80 °C | Good for extractions, low peroxide risk vs ethers like THF | Odor, limited miscibility with water |
| CPME | Petro/bio blends | 106 °C | Broad utility, low peroxide tendency | Less renewable than ethanol/2-MeTHF |
| Heptane (bio-based available) | Renewable/petro | 98 °C | Low polarity, easy recovery | VOC, flammability |
Process considerations
Prefer catalytic oxidations (e.g., TEMPO/O2) over stoichiometric chromium reagents to limit hazardous waste when converting nerol to neral/citral.
Use green protecting groups/conditions (carbonate-based, enzymatic esterifications) with recyclable solvents (supercritical CO2, green esters) where feasible.
Design for energy efficiency: many nerol transformations proceed at ambient temperature with appropriate catalysts.
Waste & safety
Terpenes are VOCs—implement condensers/scrubbers to minimize emissions; segregate peroxide-forming waste streams even if nerol itself is low-risk.
Pharmaceutical Uses
Item-specific status
Pharmacopeial status, excipient grade, and residual profiles: Not specified for this item; refer to CoA/Spec Sheet.
Literature/context (non-therapeutic)
Nerol is employed in R&D settings for fragrance/flavor profiling and as an aroma component in topical or oral-care prototypes. In such contexts, it functions as a fragrance/flavoring excipient, solvating/co-solvent aid in oil phases, or as a model monoterpene for permeation studies.
Its primary alcohol enables formation of esters (e.g., nerol acetates) used to modulate volatility and sensory profiles in formulation science.
Manufacturing/analytical considerations
Control of isomeric purity (nerol vs. geraniol) and oxidative impurities (citral) is important for sensory consistency and stability testing.
Track residual solvents and potential allergens per regulatory guidance applicable to flavors/fragrances in research prototypes. For any GMP or clinical use, procure appropriate grade and documentation; this product is for research use only.
Physical Properties
Item-specific (from Product Data)
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Literature/Reference values for nerol (for general guidance; not product specifications)
Physical state: Colorless to pale-yellow liquid with floral, rose-like odor (literature)
Boiling point: ~225–230 °C at 760 mmHg (literature)
Melting point: approximately −15 to −10 °C (literature)
Density: ~0.87–0.89 g/mL at 20–25 °C (literature)
Refractive index (nD20): ~1.46–1.47 (literature)
Vapor pressure: low; ~0.02–0.05 mmHg at 25 °C (literature)
LogP (octanol/water): ~3.2–3.6 (literature)
Water solubility: low; on the order of ~100–300 mg/L at 25 °C; miscible with many organic solvents (ethanol, diethyl ether, hexanes) (literature)
pKa (for conjugate acid of the alcohol): ~−2 (non-ionizing neutral alcohol under physiological pH; literature)
Practical notes (general)
The primary alcohol enables hydrogen bonding; however, overall hydrophobicity dominates handling behavior.
Like related terpenoid alcohols, nerol can isomerize toward geraniol under acidic conditions and may slowly oxidize to aldehydes/acids on air exposure; use minimal headspace and antioxidants if trace-peroxide formation is of concern. These are general observations; not specifications for this item.
Quality & Grades
Item-specific details
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers: Not specified for this item; refer to CoA/Spec Sheet.
Guidance on grades (general information for monoterpenoid alcohols)
Neat reagent grade: Suitable for synthesis, fragrance/flavor R&D, and analytical method development where general organic impurity limits are acceptable.
High-purity or GC-grade: Tight control on isomeric content (nerol vs. geraniol vs. linalool), oxidation products (citral, aldehydes), and residual solvents; often accompanied by detailed chromatographic profiles.
Food-/FCC-/PhEur-conforming grades: When available from suppliers, these control additional parameters (e.g., specific optical/isomer content, GC purity, residue limits). Not specified for this item.
What to verify on the CoA for nerol (recommendations)
Isomer ratio: Nerol (2Z,6E) vs. geraniol (2E,6E) and linalool; reported by GC-FID/MS.
Peroxide/aldehyde content and acid value: Indicators of oxidation; important for odor-critical or oxidation-sensitive applications.
Water content (Karl Fischer) and residual solvents: Impacts certain reactions and storage stability.
UV profile and color (APHA): For photolabile or odor applications.
Implications of stabilizers (general)
Trace antioxidant (e.g., BHT) may be used by some producers to suppress autoxidation; verify compatibility with downstream chemistry. Not specified for this item.
Reaction & Applications
Functional reactivity (general)
Primary allylic alcohol with two isolated double bonds. Reacts readily in: esterification (Fischer, Steglich), etherification, oxidation (to aldehydes—neral/citral—and acids), hydroboration–oxidation (to diols), epoxidation (Prilezhaev), dihydroxylation, and selective catalytic hydrogenation/isomerization.
Oxidation: TEMPO/BAIB or Dess–Martin to give the corresponding aldehyde (cis-citral/neral) with careful E/Z control; overoxidation to acid via Pinnick or Jones.
Protection: Formation of nerol TBDMS/TBS ethers (TBSCl, imidazole, DMF) to mask the alcohol during electrophilic alkene chemistry.
Epoxidation: mCPBA on the 2,3- or 6,7-alkenes; subsequent ring-opening gives regio-/stereodefined diols/ethers.
Hydroboration–oxidation: BH3·THF or 9-BBN followed by H2O2/NaOH affords anti-Markovnikov alcohols at the double bonds (yielding triols from stepwise application).
Cross-metathesis: With acrylates or styrenes using Grubbs II/HCAT; the allylic alcohol can coordinate—consider protection for higher yields.
Carbon–carbon formation: Allylic substitution (e.g., via nerol mesylate/tosylate) enables SN2′ chemistry to install new C–C or C–X bonds.
Application domains (non-clinical)
Fragrance/flavor research (rose-like note), natural product analog synthesis, chiral ligand/auxiliary precursors after derivatization, and as a probe in oxidation/isomerization catalysis.
Practical tips
Drying: Pass through basic alumina or treat with molecular sieves to remove water before moisture-sensitive steps.
Acid sensitivity: Mild acid can isomerize nerol to geraniol; use neutral/basic conditions and avoid strong Brønsted acids when geometry must be retained.
Oxygen/light: Work under inert gas and protect from light to minimize formation of aldehydic byproducts.
Reaction Conditions
The following are representative literature conditions for common nerol transformations (general guidance; not specifications for this item):
Oxidation to aldehyde (neral)
TEMPO (2–10 mol%), NaOCl (household bleach, pH ~8.6), KBr (cat.), EtOAc/H2O, 0–5 °C to RT, 0.5–2 h; typical isolated yields 80–90% with careful pH control.
Dess–Martin periodinane (1.3 eq), CH2Cl2, 0 °C → RT, 1–2 h; 75–90% yields; quench with Na2S2O3 to remove iodine species.
mCPBA (1.1–1.5 eq), NaHCO3 buffer, CH2Cl2, 0 °C → RT, 1–4 h; epoxide distribution depends on conditions; separate regioisomers by chromatography.
Hydroboration–oxidation
9-BBN (1.1 eq per C=C), THF, 0 °C → RT, 1–3 h; then H2O2/NaOH workup; provides anti-Markovnikov alcohols; overall 60–85% yields per alkene.
Allylic substitution (via carbonate)
Form allyl carbonate (e.g., nerol + chloroformate/NEt3), then Pd(PPh3)4 (2–5 mol%), soft nucleophile (malonate, amine), THF or toluene, RT–60 °C, 2–8 h; 60–90% yields.
Hydrogenation/isomerization
H2 (1–5 bar), Pd/C (5–10 wt%), EtOH or EtOAc, RT–40 °C, 1–4 h; stepwise saturation possible; monitor to prevent over-reduction of both double bonds.
Note: Choose solvent and protection strategy to avoid acid-promoted E/Z isomerization of the 2–3 double bond.
Safety & Handling
Item-specific hazard data
Signal Word: Not specified for this item; refer to SDS.
H-Statements: Not specified for this item; refer to SDS.
GHS Classification/Pictograms: Not specified for this item; refer to SDS.
General safety considerations for nerol and related terpenoid alcohols (literature; not item-specific)
May cause skin and eye irritation and can be sensitizing to skin in susceptible individuals. Avoid inhalation of concentrated vapors.
Combustible liquid; keep away from ignition sources. Use in well-ventilated areas or fume hood.
Potential environmental hazard to aquatic life at high concentrations; avoid release to the environment.
Handling & PPE
Wear appropriate PPE: safety glasses or goggles, lab coat, and nitrile gloves. Use secondary containment for bulk transfers.
Avoid strong acids, strong oxidizers, and light/air exposure that may promote oxidation or isomerization.
First-aid overview (consult SDS for definitive guidance)
Skin/eye contact: Rinse with water for several minutes; remove contaminated clothing; seek medical attention if irritation persists.
Inhalation: Move to fresh air; obtain medical attention if symptoms occur.
Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
Fire safety
Suitable extinguishing media: CO2, dry chemical, or foam. Cool containers with water spray.
Combustion may produce CO/CO2 and acrid fumes. Use SCBA in enclosed fires.
Solvent Selection
Nerol is generally used as a reagent/building block or aroma component rather than as a bulk solvent.
Applicability
Not typically employed as a reaction solvent due to its reactivity (allylic alcohol, dienic structure) and relatively high boiling point.
Polarity/miscibility (literature)
Moderately nonpolar, hydrogen-bond donor/acceptor via –OH.
Miscible with common organic media (ethanol, ethers, esters, hydrocarbons); low solubility in water.
When to choose nerol in a medium
As a co-substrate or substrate in biotransformations or selective oxidations where solvent and reactant coincide.
In flavor/fragrance R&D where matrix effects of the neat substance are studied.
Alternatives for use as solvent or carrier (general guidance)
For nonpolar reactions: heptane, toluene, or greener options like 2-methyltetrahydrofuran (2-MeTHF) depending on compatibility.
For protic media: ethanol or isopropanol provide similar solvency without introducing allylic unsaturation that can react.
Practical tip
If nerol must act as both solvent and substrate, control oxygen and acidity to limit isomerization to geraniol and oxidation to citral.
Storage & Reconstitution
Item-specific
Storage Conditions: Room temperature (per Product Data). Store tightly closed in a cool, dry, well-ventilated place away from heat/sparks and direct light.
Reconstitution: Not applicable; supplied neat. If a solution is required, prepare in a compatible solvent (e.g., ethanol, hexane, ethyl acetate) immediately before use.
Appearance on receipt: Not specified for this item; refer to CoA/Spec Sheet.
General stability guidance (literature; not product specifications)
Protect from air and light to minimize slow oxidation to aldehydes/acids and isomerization toward geraniol under acidic traces.
For long-term storage or sensitive applications, consider amber glass, inert gas blanket (N2/Ar), and minimal headspace. Avoid contact with strong acids/oxidizers and catalytic metals that may promote isomerization/oxidation.
If crystallization/phase separation occurs at low temperature, gently warm to ambient and mix thoroughly before use; verify composition by GC or 1H NMR if critical.
Freeze–thaw
Not typically applicable to neat liquids; if stored as solutions, avoid repeated freeze–thaw by aliquoting.
Structure & Identity
Nerol (SKU N101447) is a monoterpenoid primary alcohol and the cis-geometry isomer of geraniol.
Item-specific (from Product Data)
CAS: 106-25-2
PubChem CID: 643820
InChIKey: 105540 (as provided)
Storage: Room temperature
Shipping: Normal
Research Use: For research use only
Literature/Reference identity (general chemistry information; not item-specific)
A linear C10 monoterpene backbone bearing two isolated alkenes (at C2–C3 and C6–C7) and a terminal primary alcohol (C1–OH).
Stereochemistry: Z configuration about the C2–C3 double bond; E about the C6–C7 double bond.
Functional groups: Primary alcohol; two trisubstituted alkenes; allylic positions adjacent to both double bonds.
2D depiction in words: HO–CH2–C(=C(Z)–CH2–CH2–C(=C(E)–CH3)–CH3)–CH3 with methyl branches at C3 and C7 typical of 3,7-dimethyl-2,6-octadienyl motif.
Synthetic Utility
Retrosynthetic value
Nerol serves as a versatile C10 isoprenoid synthon. Its terminal primary alcohol allows straightforward activation (mesylate/tosylate/carbonate) for SN2/SN2′ and cross-coupling after conversion to suitable partners (e.g., allylic carbonates for Tsuji–Trost).
Key transformations (literature)
Tsuji–Trost allylation: π-Allyl Pd complexes from nerol-derived carbonates enable enantioselective allylations using chiral ligands.
Oxidation sequence: Nerol → neral (cis-citral) → Wittig/HWE olefinations to extend the conjugation or introduce functional handles.
Epoxidation/opening: Selective epoxidation at C2–C3 followed by regioselective nucleophilic opening furnishes 1,2-diols or 1,3-diols after rearrangement.
Protection–functionalization: Silyl protection of –OH permits selective functionalization of alkenes (e.g., hydroformylation, hydroboration) without competing acylation/esterification.
Radical additions: Thiol–ene or photoredox-mediated Giese additions across the alkenes to diversify side chains.
Stereochemical considerations
Maintaining the Z-geometry at C2–C3 requires neutral/basic conditions; acid-promoted isomerization can erode stereodefined products.
Practical notes
Pre-drying and oxygen exclusion reduce byproduct formation in sensitive steps (metathesis, low-valent metal catalysis).
Analytical: Track E/Z purity by GC or 1H NMR (diagnostic vinyl proton coupling constants).
Target Specificity
This product is a small-molecule monoterpenoid reagent and does not possess “target specificity” in the sense used for biological affinity reagents (e.g., antibodies, ligands). No antigen/epitope, clone, or species reactivity applies.
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