544-62-7

Basic information

• Product Name: Batyl alcohol
• Synonyms: 1,2-Propanediol,3-(octadecyloxy)-;1-o-octadecylglycerol;2,3-Dihydroxy-1-oc-tadecyloxypropane;2-Propanediol,3-(octadecyloxy)-1;3-(octadecyloxy)-2-propanediol;alpha-octadecyletherofglycerol;C.1.Batylalcohol;Glycerine1-monostearylether
• CAS NO: 544-62-7
• Molecular Formula: C₂₁H₄₄O₃
• Molecular Weight: 344.58
• EINECS: 208-874-7
• Product Categories: Inhibitors
• Mol File: 544-62-7.mol
• Article Data: 18

Chemical Properties

• Melting Point: 71-73 °C(lit.)
• Boiling Point: 419.64°C (rough estimate)
• Flash Point: 238.7 °C
• Appearance: /
• Density: 0.9975 (rough estimate)
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.5192 (estimate)
• Storage Temp.: -15°C
• Solubility: Chloroform (Slightly), Methanol (Slightly, Heated)
• PKA: 13.68±0.20(Predicted)
• Merck: 14,1011
• BRN: 1725677
• CAS DataBase Reference: Batyl alcohol(CAS DataBase Reference)
• NIST Chemistry Reference: Batyl alcohol(544-62-7)
• EPA Substance Registry System: Batyl alcohol(544-62-7)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• RTECS: TZ0960000
• Hazardous Substances Data: 544-62-7(Hazardous Substances Data)

Usage

Uses

Batyl Alcohol is used to synthesize amphiphilic alkylglycerolipids with antitumor activities. It is also used in cosmetic compounds for prevention or treatment of erythema or dermatitis or promotion of wound healing.

Definition

ChEBI: An alkylglycerol that is glycerol in which one of the primary hydroxy groups has been converted to the corresponding octadecyl ether. It is used in cosmetics as a stabilising ingredient and skin-conditioning agent.

Purification Methods

Batyl alcohol crystallises from aqueous Me2CO, EtOH or pet ether (b 40-60o). [Taguchi & Armarego Med Res Rev 18 pp43-88 1998, Beilstein 1 IV 2758.]

InChI:InChI=1/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/t21-/m1/s1

Synthetic route

4-(n-octadecyloxymethyl)-2,2-dimethyl-1,3-dioxolane (16725-43-2) → batyl alcohol (544-62-7)

Conditions	Yield
With hydrogenchloride In water for 4h; Reflux;	96%
With hydrogenchloride; methanol for 1h; Heating; Yield given;
With sulfuric acid In tetrahydrofuran at 100℃; for 2h;

Methyl stearate (112-61-8) + glycerol (56-81-5) → batyl alcohol (544-62-7) + 2-octadecyloxy-propane-1,3-diol (927-18-4)

Conditions	Yield
With 5%-palladium/activated carbon; camphor-10-sulfonic acid; hydrogen at 120℃; under 37503.8 Torr; for 16h; Autoclave; regioselective reaction;	A 73% B n/a

1-[(prop-2'-en-1'-yl)oxy]octadecane (25580-78-3) → batyl alcohol (544-62-7)

Conditions	Yield
With cethyltrimethylammonium permanganate In dichloromethane at 20℃; for 5h; Addition;	65%
With Perbenzoic acid; chloroform at 70 - 80℃; beim folgenden Hydrolyse mit wss.-alkoh.H2SO4 oder KOH;
With formic acid; sulfuric acid; dihydrogen peroxide Erwaermen des Reaktionsprodukts mit wss.-aethanol.Kalilauge;
With dihydrogen peroxide; acetic acid at 70 - 80℃; beim folgenden Hydrolyse mit wss.-alkoh.H2SO4 oder KOH;

1-monooleoyl glycerol (111-03-5, 2716-53-2, 30836-40-9, 34487-30-4, 69483-90-5, 99297-71-9, 129784-87-8) + glycerol (56-81-5) → batyl alcohol (544-62-7) + 2-octadecyloxy-propane-1,3-diol (927-18-4)

Conditions	Yield
With 5%-palladium/activated carbon; hydrogen at 120℃; under 37503.8 Torr; for 16h; Autoclave; regioselective reaction;	A 35% B n/a

octadecanoic acid 2,3-dihydroxypropyl ester (22610-63-5) + glycerol (56-81-5) → batyl alcohol (544-62-7) + 2-octadecyloxy-propane-1,3-diol (927-18-4)

Conditions	Yield
With 5%-palladium/activated carbon; hydrogen at 120℃; under 37503.8 Torr; for 16h; Autoclave; regioselective reaction;	A 34% B n/a

stearic acid (57-11-4) + glycerol (56-81-5) → batyl alcohol (544-62-7)

Conditions	Yield
With 5%-palladium/activated carbon; camphor-10-sulfonic acid; hydrogen at 20 - 140℃; under 37503.8 Torr; for 24h; Autoclave;	30%
With palladium on activated charcoal; hydrogen at 120℃; under 37503.8 Torr; for 16h; Autoclave; Inert atmosphere;	29%

1-octadecyl methanesulfonate (31081-59-1) + (R,S)-2,2-dimethyl-1,3-dioxolane-4-methanol (100-79-8) → batyl alcohol (544-62-7)

Conditions	Yield
(i) K, benzene, (ii) /BRN= 1913366/, (iii) aq. HCl, MeOH; Multistep reaction;

n-octadecyl p-toluenesulfonate (3386-32-1) + (R,S)-2,2-dimethyl-1,3-dioxolane-4-methanol (100-79-8) → batyl alcohol (544-62-7)

Conditions	Yield
(i) NaNH2, toluene, (ii) /BRN= 2011780/, (iii) aq. AcOH; Multistep reaction;

1,2-bis-octadecanoyloxy-3-octadecyloxy-propane (923-62-6) → batyl alcohol (544-62-7)

Conditions	Yield
With sodium hydroxide In methanol; chloroform

n-octadecyl p-toluenesulfonate (3386-32-1) + (2,2-dimethyl-[1,3]dioxolan-4-yl)-methanol; sodium salt (33145-48-1) → batyl alcohol (544-62-7)

Conditions	Yield
(i) NaNH2, toluene, (ii) /BRN= 2011780/, toluene, (iii) aq. HCl, EtOH; Multistep reaction;

4,4'-(3-heptadecyl-2,4-dioxa-pentane-1,5-diyl)-bis-[1,3]dioxolan-2-one → batyl alcohol (544-62-7)

Conditions	Yield
(i) AcCl, (ii) Et3N, (iii) H2, NaHCO3, PtO2, Et2O; Multistep reaction;

octadecyl glycidyl ether (16245-97-9) → batyl alcohol (544-62-7)

Conditions	Yield
With perchloric acid In 1,4-dioxane; water pH 2;

glycerol-1-octadecyl ether-2.3-isopropylidene ether → batyl alcohol (544-62-7)

Conditions	Yield
With acetic acid

O1,O2-isopropyliden-O3-octyl-glycerol → batyl alcohol (544-62-7)

Conditions	Yield
With acetic acid Erwaermen des Reaktionsprodukts mit wss.Natronlauge;
With hydrogenchloride

monosodium glycerate + sodium octadecyl sulfate → batyl alcohol (544-62-7)

Conditions	Yield
With glycerol at 210 - 215℃;
With glycerol at 210 - 215℃;

methanol (67-56-1) + batyl alcohol-3-O-α-L-fucoside → (3S,4R,5S,6S)-2-methoxy-6-methyltetrahydro-2H-pyran-3,4,5-triol (65310-00-1) + batyl alcohol (544-62-7)

Conditions	Yield
With sulfuric acid for 6h; Hydrolysis; methylation; etherification; Heating;	A n/a B 12 mg

α-O-(1-Octadecenyl)-β,α'-distearoyl-glycerin (1116-44-5) → batyl alcohol (544-62-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: H2 / Pd / cyclohexane 2: aq. NaOH / CHCl3; methanol View Scheme

1-Bromooctadecane (112-89-0) → batyl alcohol (544-62-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: tetrabutylammonium bromide; potassium hydroxide / 18 h / 35 - 40 °C 2: 903 mg / p-toluenesulfonic acid / tetrahydrofuran; H2O / Heating View Scheme
Multi-step reaction with 2 steps 1: NaH / dimethylformamide / 6 h / 60 °C 2: aq. H2SO4 / tetrahydrofuran / 2 h / 100 °C View Scheme
Multi-step reaction with 2 steps 1: sodium hydride / toluene / Inert atmosphere; Schlenk technique; Reflux 2: hydrogenchloride / water; methanol / 2 h / Inert atmosphere; Schlenk technique; Reflux View Scheme

n-octadecyl p-toluenesulfonate (3386-32-1) → batyl alcohol (544-62-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 75 percent / NaH / tetrahydrofuran 2: aq. p-TsOH / tetrahydrofuran / Heating View Scheme
Multi-step reaction with 2 steps 1: NaH / dimethylformamide; petroleum ether / 50 °C 2: 1N HCl / dioxane / Heating View Scheme

1-octadecanol (112-92-5) + CS2 → batyl alcohol (544-62-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 73 percent / 48 percent aq. NaOH / TBAB / hexane / 6 h / 45 °C 2: 65 percent / cetyltrimethylammonium permanganate / CH2Cl2 / 5 h / 20 °C View Scheme

1-octadecanol (112-92-5) → batyl alcohol (544-62-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: K2CO3 / benzene / 5 h / Heating 2: perchloric acid / dioxane; H2O / pH 2 View Scheme
Multi-step reaction with 3 steps 1: 76 percent / pyridine / 5 h / Ambient temperature 2: 1.) KOH / 1.) xylene, 1h, reflux; 2.) xylene, 5h, reflux 3: HCl/methanol / 1 h / Heating View Scheme
Multi-step reaction with 2 steps 1: Py 2: (i) K, benzene, (ii) /BRN= 1913366/, (iii) aq. HCl, MeOH View Scheme
Multi-step reaction with 3 steps 1.1: sodium hydroxide / neat (no solvent) / 7 h / 70 °C 1.2: 255 1.3: 255 2.1: 1,3-dimethylimidazolim iodide / toluene / 5 h 3.1: sodium hydroxide; ethanol View Scheme

1-octadecyl methanesulfonate (31081-59-1) → batyl alcohol (544-62-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) KOH / 1.) xylene, 1h, reflux; 2.) xylene, 5h, reflux 2: HCl/methanol / 1 h / Heating View Scheme
With hydrogenchloride; potassium hydroxide In methanol; dimethyl sulfoxide

1-chlorooctadecane (3386-33-2) → batyl alcohol (544-62-7)

Conditions	Yield
Multi-step reaction with 2 steps 2: H2O2; glacial acetic acid / 70 - 80 °C / beim folgenden Hydrolyse mit wss.-alkoh.H2SO4 oder KOH View Scheme

n-iodooctadecane (629-93-6) → batyl alcohol (544-62-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 60 - 65 °C 2: H2O2; glacial acetic acid / 70 - 80 °C / beim folgenden Hydrolyse mit wss.-alkoh.H2SO4 oder KOH View Scheme

2,3-dibutyroil-1-O-octadecyl glycerol (1198155-32-6) → batyl alcohol (544-62-7) + 2-butyroyl-1-O-octadecyl glycerol + butyric acid (107-92-6)

Conditions	Yield
Stage #1: 2,3-dibutyroil-1-O-octadecyl glycerol With pancreatin; sodium cholate; sodium cholate; sodium chloride; calcium chloride at 37℃; for 1h; pH=6.5 - 7.2; Trizma-maleate buffer; Stage #2: With hydrogenchloride In water

1-O-benzoyl3-O-octadecyl-sn-glycerol (40630-77-1, 113723-74-3) → batyl alcohol (544-62-7)

Conditions	Yield
With ethanol; sodium hydroxide

batyl alcohol (544-62-7) + trityl chloride (76-83-5) → 1-octadecyloxy-3-trityloxy-propan-2-ol (86334-56-7)

Conditions	Yield
With pyridine for 48h; Ambient temperature;	100%
With pyridine at 70℃; for 24h;	96%
With pyridine

batyl alcohol (544-62-7) + tert-butyldimethylsilyl chloride (18162-48-6) → <(tert-butyl)dimethylsilyl>oxy-1-(octadecyloxy)-3-propanol-2 (115945-64-7)

Conditions	Yield
With 1H-imidazole In N,N-dimethyl-formamide for 24h; Ambient temperature;	100%
With 1H-imidazole 1.) THF, reflux, 5 min, 2.) THF, reflux, 24 h; Yield given. Multistep reaction;

batyl alcohol (544-62-7) + acetyl chloride (75-36-5) → 1-O-octadecyl-2,3-diacetylglycerol (21994-81-0)

Conditions	Yield
at 140℃; for 0.0833333h; Inert atmosphere; Sealed tube;	93%

vinyl acetate (108-05-4) + batyl alcohol (544-62-7) → 1-O-octadecyl-3-acetylglycerol

Conditions	Yield
With immobilised Candida antarctica lipase In chloroform at 0 - 4℃; for 2h;	91%

vinyl acetate (108-05-4) + batyl alcohol (544-62-7) → 1-O-octadecyl-2,3-diacetylglycerol (21994-81-0)

Conditions	Yield
With immobilised Candida antarctica lipase at 65℃; for 17h;	90%

2,3-dimethoxythiophene (51792-34-8) + batyl alcohol (544-62-7) → 2-[(octadecyloxy)methyl]-2,3-dihydrothieno[3,4-b][1,4]dioxine (1409917-62-9)

Conditions	Yield
With toluene-4-sulfonic acid In toluene for 72h; Reflux;	88%

batyl alcohol (544-62-7) + 10-phenyl-10-hydroxy-9-anthracenone (5146-30-5) → 1-Octadecyloxy-3-tritylonoxy-2-propanol (77588-21-7)

Conditions	Yield
With toluene-4-sulfonic acid In benzene for 22h; Heating;	67.5%

batyl alcohol (544-62-7) → (octadecyloxy)methyl formate

Conditions	Yield
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; tetrabutylammomium bromide; 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃; for 4h; Time; Inert atmosphere;	66%

batyl alcohol (544-62-7) + p-toluenesulfonyl chloride (98-59-9) → 2-hydroxy-3-(octadecyloxy)propyl p-toluenesulfonate (86541-07-3)

Conditions	Yield
With pyridine In dichloromethane for 48h; Ambient temperature;	55%
With pyridine

batyl alcohol (544-62-7) → 1-[(prop-2'-en-1'-yl)oxy]octadecane (25580-78-3)

Conditions	Yield
With ammonium perrhenate; zinc In benzene at 150℃; for 24h; Inert atmosphere; Sealed tube;	47%
With ammonium perrhenate; benzyl alcohol In toluene at 150℃; for 24h; Sealed tube; regioselective reaction;	83 %Spectr.
With ammonium perrhenate; 2,4-dimethyl-3-pentanol In toluene at 140℃; for 24h; Sealed tube; regioselective reaction;	73 %Chromat.

n-dodecanoyl chloride (112-16-3) + batyl alcohol (544-62-7) → 1-O-octadecyl-3-O-lauroyl-rac-glycerol (182277-36-7)

Conditions	Yield
With pyridine In chloroform for 1h; Ambient temperature;	41%

Lawessons reagent (19172-47-5) + batyl alcohol (544-62-7) → 2-(4-Methoxy-phenyl)-4-octadecyloxymethyl-[1,3,2]dioxaphospholane 2-sulfide

Conditions	Yield
In toluene at 100℃; for 3h;	37.85%

batyl alcohol (544-62-7) + bromo-triphenyl-methane (596-43-0) → 1-octadecyloxy-2,3-bis-trityloxy-propane (118477-26-2)

Conditions	Yield
With pyridine
With pyridine

batyl alcohol (544-62-7) + 1-octadecyl methanesulfonate (31081-59-1) → 19-oxaheptatriacontane (6297-03-6)

Conditions	Yield
With potassium hydroxide In xylene Heating;

batyl alcohol (544-62-7) + 1-octadecyl methanesulfonate (31081-59-1) → 1,2,3-tri(octadecyloxy)propane (6076-42-2)

Conditions	Yield
With potassium hydroxide In xylene Heating;

batyl alcohol (544-62-7) + 1-octadecyl methanesulfonate (31081-59-1) → 1,3-bis(octadecyloxy)-2-propanol (18794-74-6)

Conditions	Yield
With potassium hydroxide In xylene Heating;

batyl alcohol (544-62-7) → octadecan-1-yloxyacetaldehyde (60956-72-1)

Conditions	Yield
With sodium periodate In methanol
(i) aq. NaIO4, CHCl3, EtOH, (ii) aq. AcOH; Multistep reaction;
With sodium periodate In water; acetone for 1.5h; Ambient temperature;

batyl alcohol (544-62-7) → 1-octadecyloxy-3-stearoyloxy-propan-2-ol (96235-95-9)

Conditions	Yield
In pyridine; chloroform (monoacylation);

batyl alcohol (544-62-7) → 1-O-Octadecyl-3-O-benzoyl-2-propanon (29909-05-5)

Conditions	Yield
(i) (benzoylation), (ii) DCC, DMSO, CF3CO2H; Multistep reaction;

batyl alcohol (544-62-7) + acetic anhydride (108-24-7) → 1-O-octadecyl-2,3-diacetylglycerol (21994-81-0)

Upstream product

• 25580-78-3 1-[(prop-2'-en-1'-yl)oxy]octadecane 
• 31081-59-1 1-octadecyl methanesulfonate 
• 100-79-8 (R,S)-2,2-dimethyl-1,3-dioxolane-4-methanol 
• 3386-32-1 n-octadecyl p-toluenesulfonate 
• 923-62-6 1,2-bis-octadecanoyloxy-3-octadecyloxy-propane 
• 16725-43-2 4-(n-octadecyloxymethyl)-2,2-dimethyl-1,3-dioxolane 
• 67-56-1 methanol 
• 120996-02-3 batyl alcohol-3-O-α-L-fucoside 
• 1116-44-5 α-O-(1-Octadecenyl)-β,α'-distearoyl-glycerin 
• 57-11-4 stearic acid 
• 56-81-5 glycerol 
• 40630-77-1 1-O-benzoyl3-O-octadecyl-sn-glycerol 
• 112-61-8 Methyl stearate 
• 111-03-5 1-monooleoyl glycerol 

Downstream Products

• 86334-56-7 1-octadecyloxy-3-trityloxy-propan-2-ol 
• 6297-03-6 19-oxaheptatriacontane 
• 6076-42-2 1,2,3-tri(octadecyloxy)propane 
• 18794-74-6 1,3-bis(octadecyloxy)-2-propanol 
• 29909-05-5 1-O-Octadecyl-3-O-benzoyl-2-propanon 
• 77588-21-7 1-Octadecyloxy-3-tritylonoxy-2-propanol 
• 133281-07-9 2-Benzyloxymethyl-4-octadecyloxymethyl-[1,3]dioxolane 
• 83526-72-1 3-O-Acetyl-1-O-octadecyl-sn-glycerin 
• 10152-41-7 1-O-octadecyl-2,3-diacetoyl-sn-glycerol 
• 18330-40-0 (S)-1-O-octadecyl-2,3-diacetylglycerol 
• 83526-75-4 (S)-1-O-octadecyl-3-acetylglycerol 
• 85712-13-6 1-O-octadecyl-3-acetylglycerol 
• 137063-73-1 1-O-octadecyl-2-O-acetyl-3-O-(4-methoxy trityl)Sn glycerol 
• 74389-69-8 1-O-octadecyl-2-acetyl-sn-glycero-3-phosphocholine 

Relevant articles and documents

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