557-61-9

Basic information

• Product Name: 1-Octacosanol
• Synonyms: Octacosanol,95%;octacosan-1-ol;1-OCTACOSANOL 93+%;Policosanol90-98%;Octacosanol10-90%;Octacosanol40-70%;OCTACOSANOL,POWDER;OCTACOSANOL, 1-(P)
• CAS NO: 557-61-9
• Molecular Formula: C₂₈H₅₈O
• Molecular Weight: 410.76
• EINECS: 209-181-2
• Product Categories: Miscellaneous;1-Alkanols;Biochemistry;Higher Fatty Acids & Higher Alcohols;Monofunctional & alpha,omega-Bifunctional Alkanes;Monofunctional Alkanes;Saturated Higher Alcohols;Nutritional fortification substances;Reduce Hypertension;Fatty AlcoholsNutrition Research;Biochemicals Found in Plants;Fatty Acids;Other Biochemical;Saturated fatty acids and derivatives;Fatty Acid Derivatives & Lipids;Glycerols;Intermediates & Fine Chemicals;Pharmaceuticals;Pesticide intermediates;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
• Mol File: 557-61-9.mol
• Article Data: 14

Chemical Properties

• Melting Point: 81-83°C
• Boiling Point: 200-250°C
• Flash Point: 135.3 °C
• Appearance: White/Crystalline Powder or Flaked Crystals
• Density: 0.8681 (rough estimate)
• Vapor Pressure: 3.99E-09mmHg at 25°C
• Refractive Index: 1.4559 (estimate)
• Storage Temp.: 2-8°C
• Solubility: Acetonitrile (Slightly, Heated), Benzene (Slightly, Heated), Chloroform (Slightl
• PKA: 15.20±0.10(Predicted)
• Water Solubility: <0.1 g/100 mL at 21.5℃
• Stability: Stable. Light-sensitive. Incompatible with strong oxidizing agents.
• Merck: 14,6744
• CAS DataBase Reference: 1-Octacosanol(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Octacosanol(557-61-9)
• EPA Substance Registry System: 1-Octacosanol(557-61-9)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 22-24/25-37/39-26
• Hazardous Substances Data: 557-61-9(Hazardous Substances Data)

Usage

Chemical Properties

white crystals or powder

Occurrence

Octacosanol is developed from wheat germ, sugar cane, or vegetable waxes.

Uses

A 28-carbon primary fatty alcohol commonly found in the epicuticular waxes of plants. It has shown protective effects against parkonsonism and due to its excellent tolerability and non-toxicity, octacosanol may be a promising agent for PD treatment.

Definition

ChEBI: A long-chain primary fatty alcohol that is octacosane in which a hydrogen attached to one of the terminal carbons is replaced by a hydroxy group.

General Description

White crystalline powder.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

1-Octacosanol is an alcohol. Flammable and/or toxic gases are generated by the combination of alcohols with alkali metals, nitrides, and strong reducing agents. They react with oxoacids and carboxylic acids to form esters plus water. Oxidizing agents convert them to aldehydes or ketones. Alcohols exhibit both weak acid and weak base behavior. They may initiate the polymerization of isocyanates and epoxides.

Fire Hazard

Flash point data for 1-Octacosanol are not available; however, 1-Octacosanol is probably combustible.

Purification Methods

Recrystallise it from large volumes of Me2CO. Sublime it at 200-250o/1mm instead of distilling it. [Beilstein 2 IV 1318.]

InChI:InChI=1/C28H58O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-25-26-27-28-29/h29H,2-28H2,1H3

Synthetic route

(E,Z)-octacos-10-en-1-ol (636583-59-0) → octacosyl alcohol (557-61-9)

Conditions	Yield
With hydrogen; palladium on activated charcoal In methanol under 19001.3 Torr; for 6h;	97%
With palladium 10% on activated carbon; hydrogen In tetrahydrofuran at 80℃; under 26252.6 Torr; for 4h;	89%

benzyl 1-octacosanol → octacosyl alcohol (557-61-9)

Conditions	Yield
With hydrogen; 5%-palladium/activated carbon In propan-1-ol at 90℃; under 3750.38 Torr; for 18h;	81%

benzyl octacos-10-enol → octacosyl alcohol (557-61-9)

Conditions	Yield
With hydrogen; 5%-palladium/activated carbon In propan-1-ol at 90℃; under 3750.38 Torr; for 18h;	80%

2-octacosyloxy-tetrahydro-pyran → octacosyl alcohol (557-61-9)

Conditions	Yield
With hydrogenchloride; acetic acid In tetrahydrofuran; ethanol; water at 20℃; for 16h;	80%

t-butyl-dimethyl-octacosyloxy-silane → octacosyl alcohol (557-61-9)

Conditions	Yield
With hydrogenchloride In ethanol at 72℃; for 5h;	77%

icosane (112-95-8) + n-docosane (629-97-0) + n-hexacosane (630-01-3) + Tridecane (629-50-5) + octadecane (593-45-3) + tetracosane (646-31-1) + octacosane (630-02-4) + n-triacontane (638-68-6) → 1-octadecanol (112-92-5) + n-eicosanol (629-96-9) + melissyl alcohol (593-50-0) + 1-docosanol (661-19-8) + tetracosyl alcohol (506-51-4) + hexacosyl alcohol (506-52-5) + octacosyl alcohol (557-61-9)

Conditions	Yield
Stage #1: icosane; n-docosane; n-hexacosane; octadecane; tetracosane; octacosane; n-triacontane With oxygen at 30 - 50℃; under 1575.16 Torr; for 0.5h; Stage #2: Tridecane With titanium(IV) isopropylate at 30 - 50℃; under 1575.16 - 3750.38 Torr; for 6.86667h; Stage #3: With sulfuric acid; water at 80℃; Product distribution / selectivity;	A 17.66% B 19.46% C 0.1% D 13.62% E 6.93% F 2.04% G 0.48%

...Expand

icosane (112-95-8) + n-docosane (629-97-0) + n-hexacosane (630-01-3) + octadecane (593-45-3) + tetracosane (646-31-1) + octacosane (630-02-4) + n-triacontane (638-68-6) → 1-octadecanol (112-92-5) + n-eicosanol (629-96-9) + melissyl alcohol (593-50-0) + 1-docosanol (661-19-8) + tetracosyl alcohol (506-51-4) + hexacosyl alcohol (506-52-5) + octacosyl alcohol (557-61-9)

Conditions	Yield
Stage #1: icosane; n-docosane; n-hexacosane; octadecane; tetracosane; octacosane; n-triacontane With oxygen at 30 - 50℃; under 1575.16 - 3675.37 Torr; for 3h; Stage #2: With sulfuric acid; water Product distribution / selectivity;	A 12.4% B 13.4% C 0.05% D 7.8% E 3.2% F 1% G 0.2%

...Expand

ethyl octacosanoate (6624-78-8) → octacosyl alcohol (557-61-9)

Conditions	Yield
With sodium; Petroleum ether; butan-1-ol
With lithium aluminium tetrahydride

methyl octacosanoate (55682-92-3) → octacosyl alcohol (557-61-9)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran for 1h; Heating;

sodium octacosanoate (25728-82-9) → octacosyl alcohol (557-61-9)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran Heating; Yield given;

Octacos-9-yn-1-ol (148172-69-4) → octacosyl alcohol (557-61-9)

Conditions	Yield
With hydrogen; palladium on activated charcoal In ethanol

Erythrinasinate → octacosyl alcohol (557-61-9) + trans-3-hydroxy-4-methoxycinnamic acid (537-73-5)

Conditions	Yield
With potassium hydroxide In chloroform for 1h; Heating;	A 50 mg B 8 mg

octacosanyl triacontanoate → octacosyl alcohol (557-61-9) + melissic acid (506-50-3)

Conditions	Yield
With potassium hydroxide In ethanol for 5h; Heating;

(2R,3S,4S,5R,6R)-2-Hydroxymethyl-6-octacosyloxy-tetrahydro-pyran-3,4,5-triol → octacosyl alcohol (557-61-9)

Conditions	Yield
With hydrogenchloride In methanol for 5h; Heating;

Benzoic acid (2R,3R,4S,5R,6R)-3,5-dihydroxy-2-hydroxymethyl-6-octacosyloxy-tetrahydro-pyran-4-yl ester → octacosyl alcohol (557-61-9)

Conditions	Yield
With hydrogenchloride In methanol for 5h; Heating;
Multi-step reaction with 2 steps 1: KOH / methanol / 5 h / Heating 2: HCl / methanol / 5 h / Heating View Scheme

12-hydroxydodecanoic acid (505-95-3) → octacosyl alcohol (557-61-9)

Conditions	Yield
Multi-step reaction with 4 steps 1: 90 percent / 50percent HBr / acetic acid / 5 h / Heating 2: EtONa / ethanol / 0.5 h / Heating 3: Li2CuCl4 / tetrahydrofuran / 4 h / -10 - -5 °C 4: LiAlH4 / tetrahydrofuran / Heating View Scheme

12-bromododecanoic acid (73367-80-3) → octacosyl alcohol (557-61-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: EtONa / ethanol / 0.5 h / Heating 2: Li2CuCl4 / tetrahydrofuran / 4 h / -10 - -5 °C 3: LiAlH4 / tetrahydrofuran / Heating View Scheme

→ octacosyl alcohol

Conditions	Yield
Multi-step reaction with 2 steps 1: Li2CuCl4 / tetrahydrofuran / 4 h / -10 - -5 °C 2: LiAlH4 / tetrahydrofuran / Heating View Scheme

9-decyn-1-ol (17643-36-6) → octacosyl alcohol (557-61-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) n-BuLi / 1.) HMPA. 2.) HMPA 2: H2 / Pd/C / ethanol View Scheme

1-Bromooctadecane (112-89-0) → octacosyl alcohol (557-61-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) n-BuLi / 1.) HMPA. 2.) HMPA 2: H2 / Pd/C / ethanol View Scheme

methyl adipoyl chloride (35444-44-1) → octacosyl alcohol (557-61-9)

Conditions	Yield
Multi-step reaction with 4 steps 1: 65 percent / stannic chloride / benzene / 2 h / Ambient temperature 2: BF3(OC2H5)3 / CHCl3 / Ambient temperature 3: W6 Raney nickel / ethanol / Heating 4: LAH / tetrahydrofuran / 1 h / Heating View Scheme

2-octadecylthiophene (102945-07-3) → octacosyl alcohol (557-61-9)

Conditions	Yield
Multi-step reaction with 4 steps 1: 65 percent / stannic chloride / benzene / 2 h / Ambient temperature 2: BF3(OC2H5)3 / CHCl3 / Ambient temperature 3: W6 Raney nickel / ethanol / Heating 4: LAH / tetrahydrofuran / 1 h / Heating View Scheme

6-(5-Octadecyl-thiophen-2-yl)-6-oxo-hexanoic acid methyl ester (111514-85-3) → octacosyl alcohol (557-61-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: BF3(OC2H5)3 / CHCl3 / Ambient temperature 2: W6 Raney nickel / ethanol / Heating 3: LAH / tetrahydrofuran / 1 h / Heating View Scheme

5-[2-(5-Octadecyl-thiophen-2-yl)-[1,3]dithiolan-2-yl]-pentanoic acid methyl ester (111514-96-6) → octacosyl alcohol (557-61-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: W6 Raney nickel / ethanol / Heating 2: LAH / tetrahydrofuran / 1 h / Heating View Scheme

C30H62O2 → octacosyl alcohol (557-61-9)

Conditions	Yield
With methanol; hydrogenchloride Heating / reflux;
With methanol; hydrogenchloride Heating / reflux;

BrMg(1+)*C10H20BrO(1-) + n-octadecylmagnesium chloride → octacosyl alcohol (557-61-9)

Conditions	Yield
Stage #1: BrMg(1+)*C10H20BrO(1-); dilithium tetrachlorocuprate In tetrahydrofuran at -20℃; for 0.333333h; Stage #2: n-octadecylmagnesium chloride In tetrahydrofuran at -20 - 20℃; Stage #3: With ammonium chloride In tetrahydrofuran; water

1-Bromo-11-hydroxyundecane (1611-56-9) → octacosyl alcohol (557-61-9)

Conditions

Yield

Multi-step reaction with 7 steps 1: triethylamine / dichloromethane 2: n-butyllithium; N,N,N,N,N,N-hexamethylphosphoric triamide / tetrahydrofuran 3: hydrogen; palladium 10% on activated carbon / ethyl acetate 4: pyridinium chlorochromate / dichloromethane 5: sodium hexamethyldisilazane / tetrahydrofuran 6: tetrabutyl ammonium fluoride / tetrahydrofuran 7: hydrogen; palladium 10% on activated carbon / ethyl acetate View Scheme

(11-bromoundecyloxy)(tert-butyl)diphenylsilane (172995-51-6) → octacosyl alcohol (557-61-9)

Conditions	Yield
Multi-step reaction with 6 steps 1: n-butyllithium; N,N,N,N,N,N-hexamethylphosphoric triamide / tetrahydrofuran 2: hydrogen; palladium 10% on activated carbon / ethyl acetate 3: pyridinium chlorochromate / dichloromethane 4: sodium hexamethyldisilazane / tetrahydrofuran 5: tetrabutyl ammonium fluoride / tetrahydrofuran 6: hydrogen; palladium 10% on activated carbon / ethyl acetate View Scheme

C30H44O2Si (1538660-98-8) → octacosyl alcohol (557-61-9)

Conditions	Yield
Multi-step reaction with 5 steps 1: hydrogen; palladium 10% on activated carbon / ethyl acetate 2: pyridinium chlorochromate / dichloromethane 3: sodium hexamethyldisilazane / tetrahydrofuran 4: tetrabutyl ammonium fluoride / tetrahydrofuran 5: hydrogen; palladium 10% on activated carbon / ethyl acetate View Scheme

octacosyl alcohol (557-61-9) + methanesulfonyl chloride (124-63-0) → C29H60O3S

Conditions	Yield
With triethylamine In tetrahydrofuran at 80℃;	70%

octacosyl alcohol (557-61-9) → octacosanal aldehyde (22725-64-0)

Conditions	Yield
Stage #1: octacosyl alcohol With calcium carbonate In dichloromethane at 20℃; for 0.5h; Molecular sieves (MS4A); Stage #2: With pyridinium chlorochromate In dichloromethane at 20℃; for 2h; Stage #3: In hexane; dichloromethane for 0.25h;	45.9%
With pyridinium chlorochromate Oxidation;

octacosyl alcohol (557-61-9) → octacosanol iodide (62154-80-7)

Conditions	Yield
With phosphorus; iodine

octacosyl alcohol (557-61-9) → octacosanoic acid (506-48-9)

Conditions	Yield
With chromium; acetic acid
Jones Oxidation;

octacosyl alcohol (557-61-9) + acetic anhydride (108-24-7) → octacosanol acetate (18206-97-8)

Conditions	Yield
With sodium acetate
With pyridine
In pyridine

octacosyl alcohol (557-61-9) + allylisocyanate (1476-23-9) → allyl-carbamic acid octacosyl ester (121706-85-2)

Conditions	Yield
With benzene

octacosyl alcohol (557-61-9) + (E)-3-<3-Methoxy-4-(tetrahydropyran-2-yloxy)phenyl>prop-2-enoic acid (145205-03-4) → (E)-3-[3-Methoxy-4-(tetrahydro-pyran-2-yloxy)-phenyl]-acrylic acid octacosyl ester

Conditions	Yield
With dicyclohexyl-carbodiimide In pyridine at 50 - 55℃;

octacosyl alcohol (557-61-9) → 1-bromo-octacosane (16331-21-8)

Conditions	Yield
With sulfuric acid; hydrogen bromide at 90 - 110℃;

octacosyl alcohol (557-61-9) + oleoyl chloride → octacosyl oleate

Conditions	Yield
With pyridine In tetrachloromethane Ambient temperature;

octacosyl alcohol (557-61-9) + n-hexadecanoyl chloride (112-67-4) → octacosanyl hexadecanoate

Conditions	Yield
With pyridine In tetrachloromethane Ambient temperature;

Upstream product

• 6624-78-8 ethyl octacosanoate 
• 55682-92-3 methyl octacosanoate 
• 112-95-8 icosane 
• 629-97-0 n-docosane 
• 630-01-3 n-hexacosane 
• 593-45-3 octadecane 
• 646-31-1 tetracosane 
• 630-02-4 octacosane 
• 638-68-6 n-triacontane 
• 1611-56-9 1-Bromo-11-hydroxyundecane 
• 172995-51-6 11-(tert-butyldiphenylsilyloxy)undecyl bromide 
• 1538660-98-8 C₃₀H₄₄O₂Si 
• 236754-35-1 C₃₀H₄₈O₂Si 
• 1538660-99-9 C₃₀H₄₆O₂Si 

Downstream Products

• 16331-21-8 1-bromo-octacosane 
• 4250-38-8 n-nonacosanoic acid 
• 22725-64-0 octacosanal aldehyde 
• 18206-97-8 octacosanol acetate 
• 506-48-9 octacosanoic acid 

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