Batyl Alcohol - Cosmetic grade,～70% , CAS No.544-62-7

CAS: 544-62-7 Cat. No.: B1519842 Formula: C₂₁H₄₄O₃ Peso molecolare: 344.58 Beilstein Registry Number: 1725680 Numero EC: 208-874-7

GRADE & PURITY Cosmetic grade, ～70%

Storage

Room temperature

Shipped In

Normal

Panoramica

Even at low concentrations, it has a thickening effect, moisturizing agents, emulsifiers, and anti-inflammatory properties.

Specifications

Specifiche e purezza

Cosmetic grade,～70%

Condizioni di conservazione di stoccaggio

Room temperature

Spedito in

Normal

Grado

Cosmetic grade

Nomi e identificatori

Sorrisi canonici

CCCCCCCCCCCCCCCCCCOCC(CO)O

IUPAC Name

3-octadecoxypropane-1,2-diol

InChIKey

OGBUMNBNEWYMNJ-UHFFFAOYSA-N

INCHI

1S/C21H44O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-24-20-21(23)19-22/h21-23H,2-20H2,1H3

Isomeri SMILES

CCCCCCCCCCCCCCCCCCOCC(CO)O

WGK Germania

3

RTECS

TZ0960000

Peso molecolare

344.58

Beilstein

1725680

Reaxy-Rn

1725677

Reaxys-RN_link_address

https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1725677&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Classe Glycerolipids
      • Subclass Monoradylglycerols

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Classe: Glycerolipids
• Subclass: Monoradylglycerols
• Intermediate Tree Nodes: Not available
• Direct Parent: Monoalkylglycerols
• Alternative Parents: 1-O-alkylglycerols Glycerol ethers Secondary alcohols 1,2-diols Dialkyl ethers Primary alcohols Hydrocarbon derivatives
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Monoalkylglycerol - 1-o-alkylglycerol - Glycerol ether - Secondary alcohol - 1,2-diol - Ether - Dialkyl ether - Organic oxygen compound - Hydrocarbon derivative - Primary alcohol - Organooxygen compound - Alcohol - Aliphatic acyclic compound
• Descrizione: This compound belongs to the class of organic compounds known as monoalkylglycerols. These are glycerolipids containing exactly one aliphatic chain linked to the glycerol moiety. This chain is the only one linked to the glycerol.
• External Descriptors: Fatty ethers - Monoalkylglycerols

Data sources

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.

DOI: 10.1186/s13321-016-0174-y

Proprietà chimiche e fisiche

• Punto di fusione (°C): 71 °C
• Peso molecolare: 344.600 g/mol
• XLogP3: 7.600
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 20
• Exact Mass: 344.329 Da
• Monoisotopic Mass: 344.329 Da
• Topological Polar Surface Area: 49.700 Ų
• Heavy Atom Count: 24
• Formal Charge: 0
• Complexity: 221.000
• 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

Application Protocols

Item-specific, tested application protocols are not provided for this product.

General handling examples (literature/practice; for research use only)

• Organic stock preparation: dissolve at 10–100 mM in ethanol or DMSO. Warm to 40–50 °C and vortex until clear. Store aliquots tightly sealed.
• Thin-film for lipid formulations: dissolve required mass in chloroform/methanol (2:1), evaporate under reduced pressure to a uniform film, dry under high vacuum ≥2 h, then hydrate above 80 °C with buffered aqueous phase while vortexing/sonicating to disperse.
• Selective acylation (example setup): dissolve in dry CH2Cl2 (0.05–0.2 M), add Et3N (2.0 eq) and catalytic DMAP (0.1 eq), cool to 0 °C, add acyl chloride (1.1 eq) dropwise, then warm to rt and stir to completion (TLC). Work up and purify by silica gel chromatography.

Always adapt conditions to scale, equipment, and safety constraints, and consult primary literature for your specific transformation.

Biological Roles

Literature/general background (not item-specific; for research context only)

• Class: ether-linked glycerolipid (alkylglycerol). Batyl alcohol features an n-octadecyl chain at the sn-1 position of glycerol.
• Occurrence: alkylglycerols are natural constituents of marine oils (e.g., shark liver oil) and are intermediates in ether lipid biosynthesis.
• Metabolic pathway: can be converted enzymatically to 1-O-alkyl-2-acylglycerols and ether phospholipids via acyltransferases and phosphotransferases; related to biosynthesis of platelet-activating factor (PAF) analogs when phosphorylcholine is introduced at sn-3.
• Biophysical role: contributes hydrophobic anchoring in membrane-mimetic systems; useful in model membrane studies due to its defined C18 chain and ether stability compared to esters.
• Enzymatic stability: the alkyl ether resists non-specific esterase-mediated hydrolysis, enabling studies of metabolism distinct from diacylglycerols.

Important note

• No medical or clinical claims are made. Any discussion here is limited to biochemical and biophysical research contexts. Researchers should design experiments acknowledging the compound’s hydrophobicity and potential for membrane incorporation.

Buffer Applications

This product is a highly hydrophobic ether lipid and is not used as a buffer or pH control reagent.

Practical note (literature)

• For aqueous work, prepare concentrated stocks in DMSO or ethanol and dilute into buffered systems with vigorous mixing and suitable carriers (e.g., surfactants, cyclodextrins, or lipid vesicles). Adjust final organic co-solvent content (often ≤1–2% v/v) to maintain buffer function and sample compatibility.

Green Alternatives

Context

• Batyl alcohol itself is a hydrophobic ether lipid. “Greener” considerations mainly concern solvent and reagent choices during handling and synthesis, not substitution of the molecule.

Greener handling strategies (literature/guidance)

• Prefer bio-derived or safer solvents when feasible: 2-MeTHF in place of THF; cyclopentyl methyl ether (CPME) or heptane in place of toluene/hexanes; ethyl acetate or dimethyl carbonate as moderately polar alternatives to chlorinated solvents.
• Reduce chlorinated solvent use (e.g., CHCl3, DCM) by adopting MTBE/MeOH or EtOAc/EtOH systems for dissolution and thin-film preparation where performance allows.
• Employ catalytic acylation methods (enzymatic lipases, organocatalysts) to minimize activating reagents and waste.
• Use solid-supported reagents (e.g., PS-DMAP) for easier workups and reduced solvent consumption.

Illustrative comparison (literature; performance must be validated for your system)

• THF vs 2-MeTHF: similar solvating ability for acylations; 2-MeTHF offers better safety profile, partial renewability, and easier phase separation with water.
• DCM vs EtOAc: EtOAc can dissolve many lipid intermediates at elevated temperature; eliminates chlorinated waste but may require longer dissolution times.

Trade-offs

• Non-chlorinated solvents sometimes reduce solubility for long-chain lipids; modest heating and longer mixing may be necessary. Always verify purity/outcomes and adjust processes accordingly.

Pharmaceutical Uses

Item-specific (from Product Data)

• Grade: Cosmetic grade (not pharmaceutical grade)

General formulation context (literature; no therapeutic claims)

• Potential roles in R&D: hydrophobic excipient/emollient component for topical or cosmetic prototype formulations; lipid phase constituent in nanoemulsions, liposomes, or solid lipid nanoparticle research.
• Functionality: contributes to occlusivity, texture, and rheology; ether linkage enhances oxidative and hydrolytic stability relative to analogous esters.
• Regulatory/compendial status: Not specified for this item; refer to CoA/Spec Sheet and applicable regulatory references for any compendial listings.

Notes for formulators

• Verify impurity profile and any stabilizers/antioxidants with the lot CoA when developing sensitive formulations.
• Evaluate compatibility with other excipients (surfactants, fatty alcohols, triglycerides) and with packaging to avoid extraction or crystallization on storage.

Physical Properties

Item-specific (from Product Data)

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.

Literature/general values for batyl alcohol (for planning only; not item specifications)

• Physical state: waxy, hydrophobic solid or semi-solid at ambient temperature (literature)
• Melting point: typically reported ~78–82 °C (literature; values vary with purity/polymorph)
• Boiling point: very high; not commonly distilled under ambient pressure; thermal decomposition may precede bp (literature)
• Density: approximately 0.90–0.94 g/cm³ at 25 °C (literature, approximate)
• Solubility: insoluble in water; soluble in ethanol, isopropanol, acetone (limited), chloroform, dichloromethane, diethyl ether, hexanes, and oils/lipids (literature)
• Partitioning: expected high logP (>6) consistent with long-chain ether lipid (literature)
• pKa: not applicable (no acidic/basic ionizable centers in the alkyl ether/glycerol region; only neutral alcohols) (general)

Practical implications

• Warmth (40–60 °C) can assist dissolution in organic solvents and oils. Gentle heating and sonication help form clear solutions.
• Due to hydrophobicity, emulsification or co-solvent systems (e.g., ethanol + buffer, or DMSO stocks) are often employed for biological assays.

Quality and Grades

Item-specific (from Product Data)

• Grade/Purity: Cosmetic grade

What “Cosmetic grade” generally indicates (context; not a guarantee of any unstated spec)

• Intended for formulation and R&D use in personal care or topical product development settings (non-therapeutic). Emphasis on appearance, odor, and impurity profile compatible with cosmetic formulation practice.
• Typical expectations (literature/industry): controlled levels of residual solvents, color, and odor; may not include analytical guarantees required for pharmaceutical GMP use.
• UV/LC specifications, trace metals, water, and peroxide values: Not specified for this item; refer to CoA/Spec Sheet.

Implications for researchers

• Suitable for synthesis, lipid formulation studies, and materials testing where cosmetic-grade organoleptic and impurity profiles are acceptable.
• For high-sensitivity analytical applications (e.g., LC-MS standards), verify impurity profile and background by consulting the lot-specific CoA or request higher analytical grade if required.

Stabilizers/antioxidants

• Not specified for this item; refer to CoA/Spec Sheet. If present, common antioxidants in cosmetic contexts include BHT or tocopherols; confirm before use in sensitive assays.

Reaction and Applications

Applications (literature/general)

• Lipid chemistry building block: precursor to ether phospholipids (e.g., 1-O-alkyl-2-acyl-glycero-3-phosphocholines/ethanolamines) by selective acylation at sn-2 followed by phosphorylation at sn-3.
• PAF analog synthesis: alkylglycerol frameworks are used to prepare platelet-activating factor analogs via phosphorylation/choline installation and sn-2 acylation.
• Surface science/materials: hydrophobizing additive; component of model membranes and monolayers due to C18 chain.
• Cosmetic/formulation R&D: emollient/lipid phase component for stability and sensorial tuning (non-therapeutic, research use only).

Reactivity notes (general)

• The ether at sn-1 is robust to many conditions (acid/base) compared with esters; free OH groups enable selective derivatization.
• Chemoselectivity: primary OH (sn-3) is typically more reactive than the secondary OH (sn-2) in acylations and alkylations; use steric/electronic control (e.g., DMAP catalysis) for selectivity.
• Protection strategies: silyl ethers (TBDMS/TBDPS) or acetonide-type protections can differentiate hydroxyls when orthogonal selectivity is required.

Practical tips

• Drying: while not highly hygroscopic, residual moisture affects acylation/phosphorylation steps; dry under high vacuum at 40–50 °C or by azeotrope with toluene.
• Thin-film hydration: dissolve in chloroform/methanol, rotary evaporate to a thin film, and hydrate above the melting transition to prepare dispersions or liposomes.
• Analysis: monitor derivatizations by TLC (hexane/EtOAc with 1–2% AcOH; visualize with anisaldehyde or phosphomolybdic acid) and confirm by 1H/13C NMR and HRMS.

Reaction Conditions

General literature guidance (typical, not item-specific)

• Selective acylation (sn-2 preferred):
  • Solvent: CH2Cl2, toluene, or 2-MeTHF
  • Reagents: acyl chloride or anhydride; catalytic DMAP (0.05–0.2 eq) + base (pyridine or Et3N)
  • Temperature: 0 °C to rt; 2–16 h
  • Notes: primary OH is often more reactive; use sterics, protecting groups, or enzyme catalysis (lipases) to favor sn-2.
• Phosphorylation (sn-3):
  • Methods: POCl3/triester routes, phosphoramidite chemistry, or CDI-activated phosphate transfer
  • Solvent: dry CH2Cl2/THF; base: DIPEA
  • Temperature: −20 °C to rt; anhydrous conditions essential
• Tosylation/mesylation of primary OH:
  • Solvent: CH2Cl2 or pyridine
  • Reagents: TsCl or MsCl; base: pyridine/Et3N
  • Temperature: 0 °C→rt; 1–4 h
• Workup/analysis:
  • Quench with aqueous NaHCO3; extract into organic phase. Monitor by TLC (hexane/EtOAc 7:3 to 1:1) and confirm by NMR/MS.

Expected outcomes

• Yields for individual steps commonly 60–90% (literature, method-dependent). Strict drying and temperature control improve regioselectivity and minimize over-acylation.

Safety and Handling

Item-specific (from Product Data)

• GHS classification: Not specified for this item; refer to SDS.
• Signal word: Not specified for this item; refer to SDS.
• Hazard statements (H-phrases): Not specified for this item; refer to SDS.
• Pictograms: Not specified for this item; refer to SDS.
• Storage conditions: Room temperature
• Shipping: Normal

General safety guidance (literature/practice; not a substitute for the SDS)

• Expected hazards: low volatility; may cause skin/eye irritation like many long-chain alcohols/ethers. Avoid inhalation of dust/aerosols.
• PPE: lab coat, safety glasses, disposable nitrile gloves. Use in a fume hood when heating, weighing fine powders, or preparing organic solutions.
• Incompatibilities: strong oxidizers (risk of exothermic reaction/oxidation of long alkyl chain); strong acids/bases can promote ether cleavage under forcing conditions; avoid open flames when using flammable solvents for dissolution.
• First aid (overview): rinse eyes/skin with water for ≥15 min upon contact; move to fresh air after inhalation of dust/solvent vapors; seek medical attention if irritation persists. If ingested, rinse mouth—do not induce vomiting; obtain medical advice.
• Handling tips: minimize prolonged heating in air to reduce oxidation; use dry, clean glassware to prevent adventitious hydrolysis/contamination.

Always consult the product-specific SDS supplied by Aladdin Scientific for authoritative hazard and response information.

Solvent Selection

General solvent behavior (literature)

• Polarity: strongly nonpolar to amphiphilic; dominates hydrophobic interactions due to the C18 alkyl chain, with limited hydrogen-bond donor capability (two free OH groups) localized on the glycerol moiety.
• Water miscibility: essentially insoluble; forms emulsions with surfactants.
• Good solvents: ethanol, isopropanol, n-propanol, methanol (warming may be required), chloroform, dichloromethane, ethyl acetate (warm), diethyl ether, THF, toluene, hexanes, isooctane, and oils/lipids.
• Stock solutions for bioassays: DMSO or ethanol stocks (e.g., 10–100 mM) are common; dilute into media with vigorous mixing and appropriate carriers (e.g., BSA, cyclodextrins, liposomes) to avoid precipitation.

Selection tips

• For lipid extraction/formulation work: chloroform/methanol (2:1, v/v) or MTBE-based systems provide robust solubilization for thin-film hydration or liposome loading.
• For organic synthesis: toluene or THF are typical for ether-stable transformations; pyridine or DMAP-containing media assist selective acylations.
• For topical/cosmetic prototyping: blend into oils (e.g., caprylic/capric triglyceride) or fatty alcohols with gentle heat to ensure uniformity.

Comparison (guidance)

• Versus shorter-chain alkylglycerols: higher hydrophobicity and melting point; improved incorporation into hydrophobic matrices but reduced aqueous dispersibility.
• Versus diacylglycerols: ether is more hydrolytically stable; different enzymatic fate in biological systems.

Storage and Reconstitution

Item-specific (from Product Data)

• Storage conditions: Room temperature
• Shipped in: Normal

General guidance (literature/practice)

• Container: store in a tightly closed, light-resistant container to minimize slow oxidation. For long-term storage, consider under inert gas (N2/Ar).
• Stability: ether linkage is robust; free alcohols are stable. Prolonged exposure to air/heat can promote oxidation of the long alkyl chain—limit headspace oxygen and avoid excessive heating.
• Recommended stock solutions: prepare in ethanol, isopropanol, or DMSO. Typical concentrations 10–100 mM depending on downstream use. Warm gently (40–60 °C) and vortex/sonicate to aid dissolution.
• Aqueous use: disperse with co-solvent (≤1–2% v/v organic) and optional carriers (surfactants, cyclodextrins, or preformed liposomes). Add slowly with vigorous mixing to prevent precipitation.
• Freeze–thaw: solid material tolerates ambient storage; solutions in organic solvents should be aliquoted to avoid repeated freeze–thaw and moisture ingress.

Where specific shelf-life or stabilizer information is needed: Not specified for this item; refer to CoA/Spec Sheet.

Structure and Identity

Item-specific (from Product Data)

• SKU: B1519842
• Product name: Batyl Alcohol
• CAS: 544-62-7
• PubChem CID: 3681
• InChIKey: 257066 (as provided)
• Grade: Cosmetic grade

Literature/computed (general reference for batyl alcohol; not item-specific)

• Synonyms: 1-O-octadecylglycerol; rac-1-O-octadecylglycerol; alkylglycerol (C18)
• Molecular formula (literature): C21H44O3
• Molecular weight (literature): ~344.58 g/mol
• Canonical SMILES (literature): CCCCCCCCCCCCCCCCCCOCC(CO)O
• Structural features: glycerol backbone bearing an ether-linked n-octadecyl chain at the primary (sn-1) position; two free alcohol groups (one primary, one secondary). Typically supplied as racemate at the secondary center (no defined stereochemistry).
• 2D description: a long, linear C18 alkyl chain attached via an ether oxygen to a three-carbon glycerol unit; terminal of the glycerol has a primary hydroxymethyl and an adjacent secondary alcohol.

Notes

• Where Product Data are absent or differ, defer to the item’s CoA/Spec Sheet for definitive identity attributes.

Synthetic Utility

Literature/general guidance

• Functional group handles: two free hydroxyls (one primary, one secondary) plus a non-labile alkyl ether at sn-1 enable diverse derivatizations while maintaining the C18 hydrophobe.
• Key transformations:
  • Selective acylation: install acyl groups at sn-2 (secondary) or sn-3 (primary) using acyl chlorides/anhydrides with catalytic DMAP or enzymatic selectivity (e.g., lipase-mediated regioselectivity).
  • Phosphorylation: convert the remaining free OH to phosphate diesters (e.g., phosphocholine/ethanolamine) to access ether phospholipids.
  • Tosylation/mesylation of the primary OH followed by displacement provides access to diverse sn-3 substituents.
  • Protection: silyl ethers (TBDMS/TBDPS) or acetonide-type protection can orchestrate orthogonal manipulations.
• Stability advantages: the alkyl ether at sn-1 tolerates acidic/basic conditions that might cleave esters, allowing sequences otherwise challenging with diacylglycerols.

Retrosynthetic value

• Serves as a convergent entry to libraries of ether lipids varying only at sn-2 acyl and sn-3 headgroup. Facilitates SAR studies in membrane-active or lipid-signaling analogs without re-installing the hydrophobic tail each time.

Target Specificity

Not applicable. This product is a small-molecule lipid and is not an antibody, probe, or biologic with defined antigen/epitope specificity.

Item-specific test applications or biological targets are not specified for this item; refer to CoA/Spec Sheet if needed.