This compound belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.
External Descriptors
Not available
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
Not applicable as an assay reagent in the sense of immunoassays or imaging. No validated protocols (WB, IHC, IF, FC) or recommended dilutions are associated with this product.
For synthetic use, see Reaction Conditions for representative procedures. For analytical characterization, standard small-molecule methods apply (e.g., 1H/13C NMR, GC/LC–MS, IR).
Biological Roles
This compound is an α-branched, short-chain unsaturated fatty-acid analogue. Item-specific biological data are not provided; the following are general, literature-based considerations for molecules of this class.
Metabolic context (general):
Carboxylic acids with C6–C8 backbones can enter fatty acid metabolic pathways after activation to acyl-CoA thioesters (via acyl-CoA synthetases). α-Branched substrates may show altered rates in β-oxidation compared to linear analogues.
Terminal alkenes can be epoxidized or hydrated by oxidative enzymes in some organisms, though detailed enzymology is substrate-dependent.
Physicochemical behavior:
At physiological pH, the carboxylate form predominates (pKa ~4.8), increasing aqueous solubility and enabling interaction with cationic sites (e.g., in transport proteins or membranes) relative to the neutral acid.
Research utility:
Serves as a model compound to study structure–activity relationships of α-branched fatty acids on membrane partitioning, micelle/vesicle formation when esterified, or as a precursor to labeled probes after derivatization (e.g., amide conjugation to fluorophores).
No claims are made regarding biological activity, safety in vivo, or therapeutic relevance. Use is restricted to research and laboratory investigations. For any biological experiments, validate purity and counterion state, and confirm absence of peroxides/impurities that may confound results.
Buffer Applications
Not typically used as a buffering agent. As a monocarboxylic acid with pKa ~4.8 (literature), it has limited buffering capacity and narrow useful range near acidic pH. For robust biological or analytical buffer systems, select established buffers (e.g., acetate, citrate, MES, MOPS) tailored to your target pH.
Practical notes if acid–base behavior is incidentally leveraged:
Aqueous compatibility improves by forming its conjugate base (sodium or potassium salt). This may be useful for extractions or phase-transfer steps, but not as a controlled buffer.
For HPLC sample preparation, avoid introducing non-volatile carboxylates when using MS detection; prefer volatile acids (formic, acetic) for mobile phase modifiers.
Green Alternatives
While the compound is a substrate rather than a solvent, greener choices can be made in how it is transformed and processed.
Greener reaction media (relative to conventional DCM/DMF):
Use 2-MeTHF or CPME for metathesis and hydrosilylation instead of DCM/toluene when compatible with the catalyst.
Employ ethyl acetate or dimethyl carbonate for Steglich-type esterifications (with careful control of DMAP/DCC solubility and byproduct removal).
Switch from DMF/NMP to acetonitrile, EtOAc, or propylene carbonate in EDC/Oxyma couplings where feasible.
Catalysis and energy:
Enzymatic esterifications (lipases) in green solvents or solvent-free systems at moderate temperatures can reduce waste and avoid carbodiimides.
Continuous removal of water (Dean–Stark with bio-based 2-MeTHF) enables high conversions under milder acid catalysis.
Oxidation choices:
Prefer H2O2 (with appropriate catalysts) over stoichiometric peracids for alkene oxidations; avoid heavy-metal oxidants when possible.
Catalyst compatibility may limit solvent substitution (e.g., some Ru metathesis catalysts prefer non-coordinating solvents).
Workup and solubility of urea byproducts can be challenging in greener solvents—opt for water-soluble coupling agents (EDC) to enable aqueous washes.
Pharmaceutical Uses
No pharmacopeial or excipient status is provided for this item. It is supplied for research use only.
General, non-clinical context:
As a synthetic intermediate: α-Branched unsaturated acids are versatile feedstocks for preparing esters and amides that can serve as model lipophilic fragments, pro-moieties, or process intermediates in medicinal chemistry campaigns.
Formulation relevance (general principles):
Carboxylic acids can form salts with appropriate bases to modulate solubility and crystallinity of intermediates during process development.
Esters derived from such acids may be explored as lipophilicity-tuning groups in preclinical structure–property studies.
No therapeutic, diagnostic, or clinical application is stated or implied for SKU M970374.
Physical Properties
Item-specific physico-chemical specifications (BP, MP, density, refractive index, water, residual solvents, or spectroscopic cutoffs) are not provided in the Product Data for SKU M970374.
Appearance (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
Boiling point (literature, indicative for C7 monounsaturated acids): typically in the ca. 200–230 °C range at ambient pressure; exact value depends on isomer and purity.
Melting point (literature): many C6–C8 branched/unsaturated acids are liquids at room temperature; specific MP not located for this isomer.
Density at 20–25 °C (literature, approximate for C7 fatty-acid isomers): ~0.90–0.95 g/mL; item-specific value not established.
pKa (literature, monocarboxylic acids): ~4.8–4.9 in water at 25 °C.
LogP (literature/estimated for C7 monounsaturated acids): typically ~2.0–2.6.
Solubility (general):
Water: low to moderate due to C7 hydrophobic chain; increases at high pH as carboxylate salt.
Organic: miscible or highly soluble in polar protic (MeOH, EtOH) and many aprotic solvents (EtOAc, THF, DCM, toluene).
Refractive index (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
Important: Treat literature ranges as guidance only. For method development, rely on batch-specific CoA and measure properties under your conditions.
Quality and Grades
Grade/Purity (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
Research Use Note: For research use only.
Context for professional users:
Analytical/reagent grades: If designated (e.g., ≥98%), such specifications typically control identity (NMR/GC/IR), purity by GC/HPLC area %, and limits on common impurities (residual solvents, isomeric acids, water). Because no explicit grade is listed here, consult the lot-specific CoA for acceptance criteria relevant to your application (synthesis vs. analytical standard).
Stabilizers: None specified. Unsaturated acids are sometimes shipped without stabilizer; if low-peroxide content is critical, verify on the CoA or test (e.g., iodometric titration) and consider storing under inert gas.
UV-Vis background: If intended for chromatographic use, low UV cutoff and baseline behavior in common eluents are relevant; no item-specific data are provided.
Residual water/solvent and metal content: Not specified for this item; refer to CoA/Spec Sheet.
Practical guidance:
If performing moisture/air-sensitive couplings (e.g., acid chloride formation), you may wish to dry the acid (e.g., azeotrope with toluene) and verify acid value before use.
For quantitative analytical work, consider verifying purity by qNMR or calibrating GC response using an internal standard.
Reaction and Applications
2-Methyl-5-hexenoic acid offers orthogonal reactivity: the carboxyl group enables classic acyl chemistry, while the terminal alkene supports diverse C=C transformations. Representative uses include:
Acyl derivatization:
Esterification: Fischer esterification in ROH/H+; Steglich esterification (DCC/DMAP) under mild, anhydrous conditions; via acid chloride (SOCl2 or (COCl)2) then ROH, useful for sterically hindered alcohols.
Amide formation: EDC·HCl/HOBt or Oxyma, HATU, or DIC/DMAP couplings with amines to access α-branched enamide precursors and fatty-acid mimetics.
Anhydrides/mixed anhydrides: pre-activation for peptide-type couplings or Curtius/Schmidt sequences (after conversion to acyl azide).
Olefin transformations on the terminal C=C:
Hydroboration–oxidation (BH3·THF or 9-BBN; then H2O2/NaOH) to furnish primary alcohols distal from the acid (retaining the acid group).
Cross-metathesis and ring-closing/cross variants (Grubbs/Hoveyda catalysts) with electron-deficient or -rich partners to diversify the side chain.
Ozonolysis or oxidative cleavage (O3; or OsO4/NaIO4, Lemieux–Johnson) to generate carbonyl fragments; terminal alkenes give aldehyde/formyl fragments under standard workups.
Radical additions (thiol–ene), hydrosilylation, and Wacker-type oxidations to methyl ketones (PdCl2/CuCl/O2) on the terminal double bond.
As a chiral auxiliary handle: the α-methyl substituent can influence conformations and selectivity in downstream transformations of derived amides/esters (literature precedent with α-branched acids).
Applications span building block synthesis for surfactant-like esters, odorant/intermediate libraries, and structure–property studies of α-branched fatty-acid analogues. No medical/clinical use is implied; for research and development only.
Reaction Conditions
The following conditions are representative literature guidance for molecules of this class; optimize for your substrate and scale.
Fischer esterification: ROH (5–20 equiv) with catalytic H2SO4 or p-TsOH; reflux (MeOH: 65 °C; EtOH: 78 °C); water removal improves conversion. Typical times: 2–16 h. Workup by neutralization/extraction.
Steglich/EDC esterification: DCC (1.1–1.2 equiv) and DMAP (5–10 mol%) or EDC·HCl/Oxyma in DCM/DMF (0–25 °C). Reaction 1–12 h. Filter urea byproducts; wash with dilute acid/base as needed.
Amide couplings: HATU (1.1–1.5 equiv), DIPEA (2–3 equiv) in DMF/MeCN/DCM, 0–25 °C, 1–6 h; or EDC·HCl (1.2–1.5 equiv) + HOAt/HOOBt/Oxyma. Monitor by TLC/LC–MS.
Acid chloride formation: SOCl2 (2–5 equiv), catalytic DMF, reflux 1–3 h; remove excess under reduced pressure; use immediately.
Hydroboration–oxidation of terminal alkene: 9-BBN (1.1 equiv) in THF, 0 °C to RT, 1–2 h; then H2O2 (3 equiv), NaOH (3 equiv), 0–25 °C, 1–2 h to give primary alcohol derivatives (acid functionality retained).
Cross-metathesis: Hoveyda–Grubbs II (2–10 mol%) in toluene, DCM, or 2-MeTHF, 25–60 °C, 2–24 h under N2; remove ethylene under slight vacuum or sparging to drive equilibrium.
Ozonolysis (terminal alkene): O3 in DCM/MeOH at −78 to −40 °C to completion (blue color persists), then reductive (Me2S, PPh3) or oxidative (H2O2) workup to desired carbonyl species.
Yields are substrate- and condition-dependent; verify with small-scale trials before scale-up.
Safety and Handling
GHS hazard classification, signal word, and pictograms are not provided in the Product Data for SKU M970374. Always consult the SDS for authoritative safety information.
Likely hazards (general for aliphatic carboxylic acids with terminal alkene):
Skin/eye irritation; may cause respiratory irritation if aerosolized.
The terminal alkene can undergo peroxidation upon prolonged air/UV exposure, though risk is lower than for ethers; store tightly closed and away from light/oxidants.
Acid functionality is incompatible with strong bases (exothermic neutralization), strong oxidizers (risk of reaction), and reactive metals/carbonates (CO2 evolution).
Recommended PPE: lab coat, safety glasses, appropriate chemically resistant gloves (e.g., nitrile). Handle in a fume hood to avoid inhalation of vapors/mists.
First-aid (general):
Skin/eye contact: flush with water for ≥15 min; remove contaminated clothing; seek medical advice if irritation persists.
Inhalation: move to fresh air; seek medical attention if symptoms occur.
Ingestion: rinse mouth; do not induce vomiting; seek medical attention.
Fire-fighting: use CO2, dry chemical, or foam; water spray to cool containers.
Spills: absorb with inert material; avoid release to environment; neutralize residues cautiously with sodium bicarbonate if appropriate.
Defer to the SDS and institutional protocols for detailed storage incompatibilities, exposure limits, and waste disposal.
Solvent Selection
This product is a small-molecule building block, not a solvent. Solvent choice pertains to its use in synthesis, purification, and analysis.
Polarity considerations:
The molecule presents a polar acidic head and a hydrophobic C6 tail; it dissolves well in moderately polar organics (EtOAc, MeOH, EtOH, acetone, acetonitrile) and in aprotic ether/halogenated solvents (THF, DCM). Water solubility is limited at neutral pH but high as the carboxylate salt (pH > pKa).
Typical solvent choices by operation:
Esterification (Fischer): anhydrous ROH (MeOH/EtOH) as both solvent and reagent; remove water continuously (Dean–Stark if higher alcohols/toluene used).
Amide coupling: DMF, NMP, DCM, or MeCN with EDC/HOBt, HATU, or DIC/DMAP; for greener options see Green Alternatives.
Hydroboration-oxidation/cross-metathesis on the terminal alkene: THF, toluene, DCM; maintain anhydrous, oxygen-free conditions for metathesis.
Preparative chromatography: normal-phase silica with hexanes/EtOAc gradients; reverse-phase (C18) with ACN/H2O + 0.1% acid for analytical work when needed.
Comparison notes:
Versus long-chain fatty acids, this C7 acid is more soluble in polar organics and easier to handle at RT.
Versus dicarboxylic acids, it requires less polar media and exhibits simpler acid-base behavior, aiding extractions.
Always validate solvent compatibility with your reagents/catalysts and target reaction conditions.
Storage and Reconstitution
Storage (item-specific): Room temperature (per Product Data). Store tightly closed in a dry, well-ventilated place away from heat and oxidizers. If long-term storage is anticipated, consider an inert-gas blanket and protection from light to minimize alkene oxidation.
Shipped In: Not specified for this item; refer to CoA/Spec Sheet.
Form/appearance: Not specified; refer to CoA/Spec Sheet. Many C7 unsaturated acids are liquids at ambient temperature; warm gently if viscous before dispensing.
Reconstitution: Not applicable. If needed for solution-phase work, prepare fresh solutions in suitable anhydrous solvents (e.g., DCM, EtOAc, MeCN, THF, MeOH/EtOH) and label with concentration and date.
Stability considerations:
Avoid prolonged exposure to air/UV which may slowly form peroxidic or oxidized species at the terminal alkene; periodic peroxide testing is prudent for aged samples.
The free acid can absorb moisture; dry under vacuum if precise stoichiometry is required.
Freeze–thaw: Generally not required; if freezing for long-term storage, use airtight containers to prevent moisture ingress upon thawing.
Always consult the lot-specific CoA/SDS for definitive guidance.
Structure and Identity
A branched, terminally unsaturated monocarboxylic acid combining a carboxyl group with a terminal alkene for dual reactivity.
Functional groups: one terminal alkene (–CH2=CH– at C5–C6) and one carboxylic acid (–CO2H) at C1.
Substitution: methyl at C2 (alpha to the carboxyl), yielding a branched α-substituted fatty-acid analogue.
Stereochemistry: none (no stereocenters as drawn; alkene is terminal, so no E/Z geometry).
2D description in words: Starting from the carboxyl carbon (C1), the α-carbon (C2) bears a methyl substituent; the chain continues through C3–C4 to a terminal double bond between C5 and C6 (vinyl group). The molecule is amphiphilic: a polar acid head and a hydrophobic, lightly branched C6 tail with a reactive terminal olefin.
Notes:
All identifiers and structures given as literature/computed values unless explicitly stated as item-specific from Product Data. Consult the CoA for definitive identifiers associated with SKU M970374.
Synthetic Utility
Key functional groups and reactivity enable efficient diversification:
Carboxylic acid manifold:
Convert to acid chlorides (SOCl2, (COCl)2, catalytic DMF) for coupling to hindered nucleophiles; proceed at 0–25 °C under inert atmosphere.
Steglich esterification (DCC/DMAP) offers mild access to esters; use EDC/Oxyma for safer aqueous workups.
Curtius rearrangement via acyl azide gives isocyanates for urea/carbamate formation (handle with appropriate safety controls).
Terminal alkene manifold:
Cross-metathesis (Grubbs II/Hoveyda–Grubbs) with acrylates, styrenes, or allyl partners to extend/functionalize the side chain; tolerate many groups, but free acids may require protection (e.g., as methyl/benzyl ester) to optimize catalyst performance.
Hydrofunctionalizations: hydroboration–oxidation to primary alcohols; hydroamination (catalytic) to access branched amines from the alkene terminus; hydrosilylation followed by Tamao–Fleming oxidation for alcohols.
Oxidative cleavage (ozonolysis) to generate truncated aldehydes/acids useful in convergent routes.
Orthogonal strategy:
Protect the acid (Me/Bn/allyl ester) to exploit alkene chemistry extensively, then deprotect under orthogonal conditions (saponification, hydrogenolysis, Pd-catalyzed deallylation).
This dual-reactive scaffold streamlines route scouting: one handle for polarity/tethering (acid/amide/ester), one for rapid diversification (alkene).
Target Specificity
Not applicable. This product is a small-molecule chemical building block, not a biological targeting reagent (e.g., antibody, enzyme inhibitor standard). No antigen, epitope, clone, or species reactivity information applies.
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