This compound belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.
External Descriptors
Other Octadecanoids
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.
Certificati (CoA, COO, BSE/TSE e tabella di analisi)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Proprietà chimiche e fisiche
Peso molecolare
300.500 g/mol
XLogP3
5.600
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
16
Exact Mass
300.266 Da
Monoisotopic Mass
300.266 Da
Topological Polar Surface Area
57.500 Ų
Heavy Atom Count
21
Formal Charge
0
Complexity
229.000
Isotope Atom Count
0
Defined Atom Stereocenter Count
0
Undefined Atom Stereocenter Count
1
Defined Bond Stereocenter Count
0
Undefined Bond Stereocenter Count
0
The total count of all stereochemical bonds
0
Covalently-Bonded Unit Count
1
Calcolatori di soluzioni
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Recensioni
Recensioni dei clienti
Application Protocols
No assay application protocols (e.g., WB, IHC, IF, FC) are applicable to this small‑molecule reagent.
Practical usage notes (general):
For biochemical assays, prepare concentrated stock solutions in ethanol, isopropanol, or DMSO; vortex and warm mildly to ensure dissolution.
When adding to aqueous media, introduce slowly with vigorous mixing or pre‑form dispersions using surfactants or cyclodextrins if compatible with your system.
For materials synthesis, pre‑dry under vacuum to constant weight before stoichiometric reactions.
For any validated application procedures specific to your laboratory, consult internal SOPs and adjust solvent vehicles and concentrations accordingly.
Biological Roles
General context (literature; not product-specific claims):
Hydroxy fatty acids, including positional isomers like 8‑hydroxyoctadecanoic acid, occur in plant polyesters (cutin/suberin) and as intermediates in lipid oxidation and β‑oxidation pathways.
Enzymatic hydroxylation of saturated fatty acids (via cytochrome P450s or lipoxygenase-related oxidations followed by reduction) can yield mid‑chain hydroxy derivatives that modulate membrane properties or act as precursors to polymeric barriers in plants.
The presence of an internal hydroxyl increases hydrogen-bonding capacity, affecting micellization, monolayer packing, and interactions with proteins/lipid bilayers compared with nonhydroxylated stearates.
In microorganisms, hydroxy fatty acids can be incorporated into complex lipids (e.g., rhamnolipids, polyhydroxyalkanoates after further transformations) and may influence biofilm properties.
Biochemical handling (general):
Carboxylate activation to acyl‑CoA by acyl‑CoA synthetases enables entry into lipid metabolism; the secondary alcohol may be further oxidized to a ketone or esterified in vivo.
Ionization state: At physiological pH, the carboxylate is deprotonated, enhancing amphiphilicity; the secondary –OH remains neutral, contributing to hydrogen bonding without charge.
Note: The above summarizes literature biology of hydroxy fatty acids and does not imply any therapeutic or clinical use. This product is supplied strictly for research use in vitro or in non‑clinical applications.
Buffer Applications
This compound is a hydrophobic hydroxy fatty acid and is not typically used as a buffering agent. It lacks a conjugate acid/base pair in a pH range suitable for maintaining constant pH in aqueous systems.
Practical note: If dispersion in aqueous buffers is required (e.g., for biochemical assays), prepare stock solutions in a water‑miscible organic solvent (ethanol, DMSO) and dilute into buffer below the critical solvent fraction, or convert to an alkali metal salt to enhance dispersibility. Include appropriate vehicle controls in biological experiments.
Green Alternatives
This product is itself a fatty‑acid–based building block, often considered more sustainable than purely petrochemical analogs when sourced from biobased feedstocks. Green chemistry considerations focus on solvent choice, catalysts, and energy input rather than replacing the molecule per se.
Greener processing choices (general guidance):
Solvents: Prefer bio‑derived or lower‑toxicity solvents (EtOAc, 2‑MeTHF, CPME, dimethyl carbonate, ethanol) instead of chlorinated solvents where feasible.
Catalysis: Use organocatalysts or enzyme catalysis (lipases) for esterification/transesterification under mild conditions, reducing energy and avoiding stoichiometric reagents.
Activation: Avoid acid chlorides (SOCl2, oxalyl chloride) when possible; apply carbodiimide couplings with greener solvents or use CDI; or drive Fischer esterifications with azeotropic water removal.
Energy: Microwave or flow processing can reduce reaction times and improve efficiency.
Comparison (illustrative; not item-specific specifications):
Choice | Conventional approach | Greener alternative | Trade‑offs
--- | --- | --- | ---
Esterification | DCM + DCC/DMAP | 2‑MeTHF or EtOAc; enzyme‑catalyzed in tert‑amyl alcohol | Possible longer reaction times; enzyme cost
Workup | Chlorinated extraction | EtOAc or MTBE extraction | Solubility must be verified
Protection | TBS in DMF | Carbonate protection in EtOAc or MeTHF | Stability differences
Supply chain note: If sustainability is critical, request documentation on bio‑based content and manufacturing route.
Pharmaceutical Uses
No pharmacopeial grade or specific excipient designation is provided for this item.
Item-specific (from Product Data):
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
General formulation context (literature; not product-specific claims):
Long‑chain fatty acids and their esters are used as excipients (emollients, lubricants, surfactants) in topical or oral formulations. Hydroxy fatty acids can enhance polarity and influence rheology or crystallinity in semi‑solid bases.
Metal salts (e.g., magnesium, zinc stearates) are common lubricants; analogous salts of hydroxy‑stearates may provide modified performance, though they are less standardized.
For any use in regulated products, compliance with pharmacopeial monographs and impurity controls (residual solvents, peroxides, heavy metals) is essential—such controls are not specified for this catalog research item.
Research-use note: This product is supplied for research and laboratory use only and is not intended for human or veterinary applications.
Physical Properties
Item-specific (from Product Data):
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Molecular Formula: Not specified for this item; refer to CoA/Spec Sheet.
Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet.
Literature/general properties (for 8‑hydroxyoctadecanoic acid; values are typical references, not item specifications):
Physical state: waxy solid or low‑melting solid typical of long-chain fatty acids and their hydroxy derivatives
Melting point: commonly in the tens of °C to low hundreds °C for hydroxy-stearic acids; exact MP depends on isomer and enantiomeric composition (consult CoA for lot-specific value)
Boiling point: not practical due to decomposition at elevated temperatures; usually characterized by melting rather than boiling
Density: typically ~0.9–1.0 g/mL for molten long-chain fatty acids (temperature dependent)
Solubility: practically insoluble in water; soluble in polar organic solvents capable of H-bonding and/or acid–base interaction (e.g., ethanol, methanol, isopropanol, acetone), and in many aprotic solvents upon heating; soluble in chlorinated solvents; strong solubility in hot alcohols
Partition behavior: expected high hydrophobicity (large logP) with enhanced polarity versus stearic acid due to the additional hydroxyl group
Acidic/basic character: carboxylic acid pKa typically ~4.5–5.0 (literature for saturated fatty acids); secondary alcohol pKa ~16–17 (not ionized under neutral conditions)
Refractive index: not typically reported for solids of this class
Note: Do not treat the above as specifications. For exact, lot-specific data, refer to the CoA/Spec Sheet.
Quality and Grades
Item-specific (from Product Data):
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Shipped In: Not specified for this item; refer to CoA/Spec Sheet.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Interpretation and implications (general guidance for this compound class; not product-specific):
Purity context: For hydroxy fatty acids, typical impurities include positional isomers, unmodified fatty acids (e.g., stearic acid), residual solvents, water, and oxidative byproducts (e.g., hydroperoxides). Purity specifications often rely on GC/FID, GC–MS, or HPLC.
Acid value / hydroxyl value: Many suppliers characterize by acid number and hydroxyl number to confirm functionality. If critical to your application (e.g., polymer stoichiometry), verify these on the CoA.
Enantiomeric composition: The C8 center is chiral. Unless specified (e.g., “(R)-8‑HSA”), assume racemic. Chiral HPLC or derivatization GC can quantify ee.
Water/peroxide/metal limits: Not specified for this item; refer to CoA/Spec Sheet. If your use is peroxide‑sensitive (e.g., radical polymerizations), request recent peroxide values.
UV profile: Long-chain fatty acids generally have low UV absorbance above ~210–220 nm; for LC–UV assay work, confirm UV cutoff empirically or via CoA.
Recommendation: For analytical or formulation-critical work, request a current CoA including identification (NMR/IR/GC), purity assay, acid value, hydroxyl value, and residual solvents.
Reaction and Applications
Functional handles and typical transformations (literature/general):
Carboxyl group: esterification (Fischer, Steglich/DCC–DMAP), amidation (EDC/HOBt, HATU), acyl chloride formation (SOCl2, oxalyl chloride) for further acylation.
Secondary alcohol: esterification/carbonate formation, etherification, silyl protection (TBS/TBDPS), oxidation to ketone (e.g., Dess–Martin, PCC under controlled conditions), or conversion to halide/mesylate for substitution.
Intramolecular reactions: medium‑ring lactonization (C1→C8) under high‑dilution or Yamaguchi conditions; macrocyclization strategies can also be explored.
Polymer and materials: synthesis of telechelic or AB‑type monomers for polyesters, polyurethanes, and plasticizers; the internal –OH modulates crystallinity and thermal properties relative to stearates.
Surfactants and lubricants: partial neutralization (soaps) and selective esterification yield nonionic/anionic surfactants with tailored HLB; esters serve as biodegradable lubricants/emollients.
Asymmetric synthesis: the stereogenic C8 enables chiral derivatization studies; chiral separation or selective enzymatic acylation offers access to single enantiomers.
Surface science: long‑chain amphiphiles assemble into monolayers; 8‑HSA derivatives can be evaluated in Langmuir–Blodgett films or SAMs (when coupled to appropriate anchors).
Practical tips:
Drying: Dry under high vacuum at mild temperature; if water content matters, azeotrope with toluene or dry by co‑evaporation with anhydrous solvents.
Peroxide control: Although saturated, long heating/air exposure can introduce peroxides at the alcohol; include antioxidants (e.g., BHT) if conducting radical processes.
Purification: Recrystallization from alcohols or acetone/hexanes; for silica chromatography, suppress tailing with acidic modifiers or use pre‑silylated silica.
Reaction Conditions
The following are literature/general guidelines for common transformations of hydroxy fatty acids and are not product specifications.
Esterification of –CO2H (Fischer):
Solvent: anhydrous MeOH or EtOH; catalyst: H2SO4 (1–5 mol%) or p‑TsOH; temperature: reflux; water removal by Dean–Stark (for higher alcohols/azeotropes). Typical times: 2–16 h; monitor by TLC/GC.
Steglich esterification of secondary –OH:
Solvent: DCM, 2‑MeTHF, or EtOAc; reagents: DCC (1.1 eq) + catalytic DMAP (5–10 mol%) with desired acid; temperature: 0 °C → RT; time: 2–12 h. Filter dicyclohexylurea.
Amide formation from –CO2H:
EDC·HCl (1.1–1.5 eq) + HOBt or HOAt, base (DIPEA), solvent: DMF/DCM; RT to 40 °C; 4–18 h. Alternatively HATU for hindered amines.
Alcohol protection (TBS):
Reagents: TBSCl (1.2 eq), imidazole (3 eq); solvent: DMF; RT; 2–6 h. Remove with TBAF in THF.
Oxidation of secondary –OH → ketone:
Dess–Martin periodinane (1.3 eq), solvent: DCM; 0 °C to RT; 1–3 h. Work up with Na2S2O3/NaHCO3.
Lactonization (medium ring, C1→C8):
Yamaguchi: 2,4,6‑trichlorobenzoyl chloride (1.2 eq), Et3N, catalytic DMAP; solvent: toluene; high dilution (≤5 mM); 60–110 °C; hours to overnight. Expect modest to moderate yields typical of medium rings.
General tips:
Due to long-chain hydrophobicity, reactions benefit from efficient mixing and, where applicable, phase‑transfer catalysts.
Warm gently to maintain solubility, but avoid prolonged air exposure at elevated temperature to limit oxidation.
For analytics, methyl ester derivatives improve GC behavior of fatty acids.
Safety and Handling
Item-specific (from Product Data):
GHS Classification / Signal Word / H-Statements / Pictograms: Not specified for this item; refer to SDS.
Storage Conditions: Room temperature
General safety considerations for hydroxy fatty acids (literature/general; not product-specific):
Expected hazards: Generally low acute toxicity; may cause skin or eye irritation. Prolonged contact can lead to defatting/irritation. Dusts (if powdered) may cause mechanical irritation.
PPE: Safety glasses with side shields, lab coat, and appropriate gloves (e.g., nitrile). Use in a well‑ventilated area or fume hood during reactions, heating, or when handling powders.
Handling: Avoid breathing dust/aerosols. Prevent contact with strong oxidizers (risk of exotherm) and strong bases (will form soaps; foaming/heat possible). Avoid ignition sources when heating oils/long-chain organics.
First aid (overview):
Eye contact: Rinse cautiously with water for several minutes; remove contact lenses if present and easy; seek medical attention if irritation persists.
Skin contact: Wash with soap and water; remove contaminated clothing.
Inhalation: Move to fresh air; seek medical advice if symptoms persist.
Ingestion: Rinse mouth; do not induce vomiting; seek medical advice.
Fire safety: Combustible organic solid. Use CO2, dry chemical, or foam to extinguish. Thermal decomposition may generate irritating fumes.
Environmental: Insoluble in water; avoid release to drains. Collect spillage with absorbent.
Always consult the product’s SDS for authoritative hazard classification and response procedures.
Solvent Selection
8‑Hydroxyoctadecanoic acid is amphiphilic but predominantly hydrophobic. Solvent choice depends on whether you exploit the acid or alcohol functionality, and the need for dissolution vs suspension.
Water: practically insoluble; forms emulsions/soaps in basic aqueous media (carboxylate salts increase dispersibility).
Alcohols (MeOH, EtOH, i‑PrOH): good to excellent solubility upon warming; suitable for recrystallization, esterification, and analytical sample prep.
Polar aprotics (THF, dioxane, DMF, DMSO, NMP): typically good solubility; useful for coupling and protection chemistries.
Chlorinated (DCM, CHCl3): good solubility; common for workups and film casting.
Hydrocarbons (toluene, hexanes): limited solubility at RT; increases on heating—useful for melt reactions or azeotropic water removal.
Polarity context: Low overall polarity with localized polar sites. Hydrogen bonding enables dissolution in H‑bond donor/acceptor solvents.
Practical tips:
Warm solutions (40–60 °C) often accelerate dissolution. Avoid prolonged high‑temp exposure to air to limit oxidation.
For aqueous processing, convert to the sodium/potassium carboxylate to create micellar/soapy solutions; neutralize post‑processing if needed.
For chromatographic purification, normal‑phase silica may strongly retain the acid; add 0.1–1% AcOH to eluents or use reversed‑phase methods.
Comparison (general):
Versus stearic acid: 8‑HSA dissolves better in polar solvents due to the extra –OH and can engage in additional H‑bonding; it may crystallize differently and show higher viscosity in melts.
Storage and Reconstitution
Item-specific (from Product Data):
Storage Conditions: Room temperature
General guidance for this compound class (not item-specific specifications):
Container: Store in a tightly sealed, inert container (glass with PTFE‑lined cap) to minimize moisture and oxygen ingress.
Atmosphere: If storing long term or at elevated temperatures, consider inert gas blanket (N2/Ar) to limit oxidative changes.
Light/heat: Protect from excessive heat and direct light. Avoid prolonged storage above the melting point unless under inert atmosphere.
Stabilizers: Not specified for this item; refer to CoA/Spec Sheet. If peroxide formation is a concern for your application, test periodically or add suitable antioxidants in your process.
Reconstitution/handling:
Solvents: Dissolve in warm ethanol, isopropanol, acetone, THF, DMSO, DMF, or chlorinated solvents as needed. Insoluble in water unless converted to a salt or dispersed with surfactants.
Dispersion: For aqueous work, prepare the sodium/potassium salt by neutralization with NaOH/KOH in ethanol/water, then dilute; re‑acidify after use if the free acid is required.
Freeze–thaw: Not typically applicable to solids; if stored as a solution, avoid repeated freeze–thaw by aliquoting.
Always consult the product label and CoA/SDS for any lot‑specific storage or stability instructions.
Structure and Identity
Brief overview: 8-Hydroxyoctadecanoic acid is a monohydroxylated C18 saturated fatty acid (a hydroxy-stearic acid) bearing a terminal carboxylic acid and a secondary alcohol at C8, introducing one stereogenic center (typically supplied as racemate unless otherwise noted).
Item-specific (Product Data):
Product Name: 8-Hydroxyoctadecanoic acid
CAS: 6807-91-6
CID: 361944
InChIKey: 450536 (as provided)
Storage Conditions: Room temperature
Research Use: For research use only
Literature/computed (general identity; not item-specific specifications):
Common synonym: 8-Hydroxystearic acid
Functional groups: one carboxylic acid (–CO2H) at C1; one secondary alcohol (–OH) at C8; fully saturated aliphatic chain (no C=C)
Stereochemistry: chiral at C8 (R/S possible); if not specified, material is typically racemic
Molecular formula (literature): C18H36O3
Molecular weight (literature): ~300.48 g/mol
SMILES (representative, literature): O=C(O)CCCCCC(O)CCCCCCCCCC (one of several valid representations; stereochemistry unspecified)
2D structural description (general): A linear 18‑carbon alkyl chain with a terminal carboxyl group at one end (C1). Counting from the carboxyl carbon, the C8 methine bears a hydroxyl substituent, flanked by methylene segments on both sides, giving a long-chain amphiphile with a polar headgroup (acid + hydroxyl) and a hydrophobic tail.
Synthetic Utility
8‑Hydroxyoctadecanoic acid offers dual functionality—a carboxylic acid and a mid‑chain secondary alcohol—enabling orthogonal derivatization and construction of advanced amphiphiles and polymers.
Key reactivity (literature/general):
Bidirectional derivatization: Prepare half‑esters (at –OH) while keeping –CO2H free for amidation/esterification, or vice versa via protecting groups (TBS, benzyl) for selective sequences.
Oxidation/reduction: Secondary –OH → ketone (for subsequent Baeyer–Villiger to yield distal esters) or → halide/mesylate for SN2′‑type chain functionalization; –CO2H → alcohol (LiAlH4, BH3·THF) to yield 1,8‑octadecanediol precursors.
Macro/medium ring formation: Yamaguchi or Shiina lactonizations afford an 8‑membered lactone; high dilution minimizes oligomerization.
Surfactant scaffolds: Esterify –OH with poly(ethylene glycol) monomethyl ether (mPEG) and –CO2H with small alcohols to tailor HLB and CMC.
Urethane/amide linkages: Couple with diisocyanates or diamines to generate polyurethanes or polyamides with internal H‑bond donors/acceptors affecting Tg and crystallinity.
Retrosynthetic value:
Serves as a masked C18 synthon where mid‑chain functionality facilitates branching, cyclization, or introduction of reporter tags (e.g., azides/alkynes via mesylate → substitution pathways).
Practical: Control regioselectivity by temporary protection of one functional group; monitor conversions via IR (νOH, νC=O) and 1H/13C NMR (diagnostic shifts for adjacent CH–OH and carbonyl carbons).
Target Specificity
Not applicable. This product is a small‑molecule hydroxy fatty acid, not an antibody, enzyme, or affinity reagent. No antigen/epitope specificity, clone information, or species reactivity applies.
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