593-50-0

Basic information

• Product Name: 1-Triacontanol
• Synonyms: N-TRIACONTANOL;MYRICYLALCOHOL;MIRACULAN;TA;triacon-10;TRIACONTANOL;TRIACONTANOL, 1-;WELL-BLOOM
• CAS NO: 593-50-0
• Molecular Formula: C₃₀H₆₂O
• Molecular Weight: 438.81
• EINECS: 209-794-5
• Product Categories: Miscellaneous Natural Products;PLANT GROWTH REGULATOR;1-Alkanols;Biochemistry;Higher Fatty Acids & Higher Alcohols;Monofunctional & alpha,omega-Bifunctional Alkanes;Monofunctional Alkanes;Plant Growth Regulators;Plant Growth Trgulators (Others);Saturated Higher Alcohols;Agro-Products;Aliphatics;Pesticide intermediates;fertilizer
• Mol File: 593-50-0.mol
• Article Data: 30

Chemical Properties

• Melting Point: 86-87 °C(lit.)
• Boiling Point: 480.56°C (rough estimate)
• Flash Point: 130.12 °C
• Appearance: Slightly beige/Flakes
• Density: 0.8672 (rough estimate)
• Vapor Pressure: 1.01E-09mmHg at 25°C
• Refractive Index: 1.4604 (estimate)
• Storage Temp.: 2-8°C
• Solubility: Benzene (Slightly), Chloroform (Slightly, Heated)
• PKA: 15.20±0.10(Predicted)
• Merck: 14,9591
• BRN: 1711965
• CAS DataBase Reference: 1-Triacontanol(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Triacontanol(593-50-0)
• EPA Substance Registry System: 1-Triacontanol(593-50-0)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 593-50-0(Hazardous Substances Data)

Usage

Chemical Properties

slightly beige flakes. Soluble in most organic solvents; insoluble in water. Combustible.

Uses

Different sources of media describe the Uses of 593-50-0 differently. You can refer to the following data:
1. It was reported to be a new naturally occurring plant-growth regulator. Present in plant cuticle waxes and in beeswax as the palmitate.
2. It was reported to be a new naturally occurring plant-growth regulator. Present in plant cuticle waxes and in beeswax as the palmitate

InChI:InChI=1/C30H62O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-25-26-27-28-29-30-31/h31H,2-30H2,1H3

Synthetic route

12-Triaconten-1-ol (95855-73-5) → melissyl alcohol (593-50-0)

Conditions	Yield
With hydrogen; platinum(IV) oxide In methanol; toluene for 6h;	98%

methyl 1-triacontanoate (629-83-4) → melissyl alcohol (593-50-0)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran 1.) -10 deg C -> room temperature, 1 h, 2.) room temperature, 4 h;	96%
With lithium aluminium tetrahydride In tetrahydrofuran 1.) -10 deg C to room temperature, 1 h, 2.) room temperature, 4 h;	95%
With lithium aluminium tetrahydride In tetrahydrofuran	95%

triacont-11-yn-1-ol (79162-67-7) → melissyl alcohol (593-50-0)

Conditions	Yield
With hydrogen; palladium on activated charcoal In tetrahydrofuran for 4h;	95%

10-triacontyn-1-ol (82672-50-2) → melissyl alcohol (593-50-0)

Conditions	Yield
With hydrogen; platinum(IV) oxide In ethanol for 2h; Heating;	90%

(Z)-12-Triacontan-1-ol (131302-56-2) → melissyl alcohol (593-50-0)

Conditions	Yield
With hydrogen; palladium on activated charcoal In ethyl acetate for 8h; Ambient temperature;	90%

C36H74OSi → melissyl alcohol (593-50-0)

Conditions	Yield
Stage #1: C36H74OSi With palladium 10% on activated carbon; hydrogen In methanol at 20℃; Stage #2: With hydrogenchloride In water for 0.333333h; Solvent; Reagent/catalyst; Reflux;	90%

melissic acid (506-50-3) → melissyl alcohol (593-50-0)

Conditions	Yield
With hydrogenchloride; thionyl chloride In diethyl ether; ethanol; chloroform; ethyl acetate; acetone; benzene	86%
Multi-step reaction with 2 steps 1: H2SO4 2: sodium; butyl alcohol View Scheme

(9E,21E)-Triaconta-9,21-dienoic acid methyl ester (1001561-47-2) → melissyl alcohol (593-50-0)

Conditions	Yield
With hydrogen; Atkins' catalysator In diethylene glycol dimethyl ether at 250℃; under 152000 Torr;	80%
Multi-step reaction with 2 steps 1: H2 / PtO / 760 Torr 2: LiAlH4 / tetrahydrofuran / 3 h / Heating View Scheme

C12H24ClMgO(1-)*Cl(1-)*Mg(2+) + 1-Bromooctadecane (112-89-0) → melissyl alcohol (593-50-0)

Conditions	Yield
dilithium tetrachlorocuprate In tetrahydrofuran at -5 - 0℃; for 4h;	68%

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

15-triacontene (72443-19-7) → melissyl alcohol (593-50-0) + n-triacontane (638-68-6)

Conditions	Yield
With tert.-butylhydroperoxide; zirconocene dichloride; sodium bis(2-methoxyethoxy)aluminium dihydride 1.) THF, 96 h, 40 deg C, 2.) ClCH2CH2Cl, 1 h, room temp.; Yield given. Multistep reaction;	A n/a B 10%

Ethyl tricontanoate (7505-12-6) → melissyl alcohol (593-50-0)

Conditions	Yield
With sodium; butan-1-ol
With lithium aluminium tetrahydride In tetrahydrofuran Yield given;

1-triacontyne (61847-90-3) → melissyl alcohol (593-50-0)

Conditions	Yield
With sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; dihydrogen peroxide 1) THF, 10 h; Yield given. Multistep reaction;

n-triacontyl acetate (41755-58-2) → melissyl alcohol (593-50-0)

Conditions	Yield
saponification;
With potassium hydroxide In ethanol Yield given;

1-triacosanal (22725-63-9) → melissyl alcohol (593-50-0)

Conditions	Yield
With lithium aluminium tetrahydride In diethyl ether Yield given;

1-octadecylmagnesium bromide (92206-73-0) + 2-[(12-bromododecyl)oxy]tetrahydro-2H-pyran (112999-97-0, 88517-92-4) → melissyl alcohol (593-50-0)

Conditions	Yield
With pyridinium p-toluenesulfonate; dilithium tetrachlorocuprate 1) 0 deg C 2) methanol, heating, 4 h; Yield given. Multistep reaction;

15-triacontene (72443-19-7) → melissyl alcohol (593-50-0) + 2-hydroxytricontane (13230-67-6)

Conditions	Yield
With sodium hydroxide; borane; dihydrogen peroxide Yield given. Multistep reaction. Title compound not separated from byproducts;
With sodium hydroxide; borane; dihydrogen peroxide Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;
With sodium hydroxide; borane; dihydrogen peroxide In tetrahydrofuran; diethylene glycol dimethyl ether Product distribution;	A 36 % Chromat. B 15 % Chromat.

Triacontanyl dotriacontanoate (145204-11-1) → melissyl alcohol (593-50-0) + Lacceric acid (3625-52-3)

Conditions	Yield
With potassium hydroxide In ethanol

trans-triacontyl-4-hydroxycinnamate (120727-03-9) → melissyl alcohol (593-50-0) + p-Coumaric Acid (7400-08-0)

Conditions	Yield
With potassium hydroxide In methanol; chloroform for 2h; Heating;	A 5 mg B 10 mg

triacont-13-yn-1-ol (111301-34-9) → melissyl alcohol (593-50-0)

Conditions	Yield
With hydrogen; palladium on activated charcoal In tetrahydrofuran for 4h;

Sodium; triacontanoate (75501-00-7) → melissyl alcohol (593-50-0)

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

13-(Z)-triacontene (145315-03-3) → melissyl alcohol (593-50-0)

Conditions	Yield
With sodium hydroxide; bis(cyclohexanyl)borane; dihydrogen peroxide 1a) THF, RT, 2 h, 1b) diglyme, 48 h, reflux; Yield given. Multistep reaction;

1-benzyloxytriacontane → melissyl alcohol (593-50-0)

Conditions	Yield
With trimethylsilyl iodide In chloroform at 25℃; for 1h; Yield given;

2-Triacontyloxy-tetrahydro-pyran → melissyl alcohol (593-50-0)

Conditions	Yield
With hydrogenchloride In ethyl acetate for 4h; Ambient temperature; Yield given;

triacontyl hexadecanoate (6027-71-0) → melissyl alcohol (593-50-0) + 1-hexadecylcarboxylic acid (57-10-3)

Conditions	Yield
With potassium hydroxide In methanol Hydrolysis;

12-hydroxydodecanoic acid (505-95-3) → melissyl alcohol (593-50-0)

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) → melissyl alcohol (593-50-0)

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

methyl 11-formylundecanoate (2009-59-8) → melissyl alcohol (593-50-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: 1.) butyllithium / 1.) THF, hexane, -70 deg C, 15 min, 2.) a) -70 deg C, 5 h, b) from -70 deg to RT, 1.5 h, c) RT, 15 h 2: 90 percent / H2 / 2percent Pd-C / hexane / 120 h / Ambient temperature 3: 69 percent / lithium aluminum hydride / diethyl ether / 1.) reflux, 5 h, 2.) from 20 deg C to 25 deg C, 15 h View Scheme

1,4-dioxane-2,6-dione (4480-83-5) + melissyl alcohol (593-50-0) → C34H66O5

Conditions	Yield
With stannous octoate In chloroform Reflux; Inert atmosphere;	86.1%

melissyl alcohol (593-50-0) → n-Triacontyl bromide (4209-22-7)

Conditions	Yield
With carbon tetrabromide; triphenylphosphine In acetonitrile for 2h; Heating;	85.5%
With bromine; triphenylphosphine In dichloromethane Ambient temperature; Yield given;

succinic acid anhydride (108-30-5) + melissyl alcohol (593-50-0) → C34H66O4

Conditions	Yield
With stannous octoate In chloroform Reflux; Inert atmosphere;	82.6%

2,2'-oxybis-acetic acid (110-99-6) + melissyl alcohol (593-50-0) → C34H66O5

Conditions	Yield
With dmap; 2-chloro-1-methyl-pyridinium iodide In N,N-dimethyl acetamide at 20℃; for 12h; Inert atmosphere;	72.6%

melissyl alcohol (593-50-0) + p-Coumaric Acid (7400-08-0) → trans-triacontyl-4-hydroxycinnamate (120727-03-9)

Conditions	Yield
With dicyclohexyl-carbodiimide In dichloromethane at 25℃; for 1.5h;	70%

melissyl alcohol (593-50-0) + 1-Adamantanecarbonyl chloride (2094-72-6) → C41H76O2 (1353717-95-9)

Conditions	Yield
With triethylamine In chloroform at 20℃; for 12h; Inert atmosphere;	44%

melissyl alcohol (593-50-0) → 1-iodotriacontane (62154-82-9)

Conditions	Yield
With phosphorus; water; iodine

melissyl alcohol (593-50-0) → melissic acid (506-50-3)

Conditions	Yield
With chromium; acetic acid
With nitric acid

melissyl alcohol (593-50-0) + acetic anhydride (108-24-7) → n-triacontyl acetate (41755-58-2)

Conditions	Yield
With sodium acetate
In pyridine
With pyridine
With pyridine

melissyl alcohol (593-50-0) → 1-chlorotriacontane (62016-82-4)

Conditions	Yield
With phosphorus pentachloride

Upstream product

• 629-83-4 methyl 1-triacontanoate 
• 41755-58-2 n-triacontyl acetate 
• 6027-71-0 triacontyl hexadecanoate 
• 116577-41-4 sodium salt of 12-bromododecanoic acid 
• 18202-10-3 11-dodecyn-1-ol 
• 629-93-6 n-iodooctadecane 
• 629-89-0 1-octadecyne 
• 112-88-9 octadec-1-ene 
• 18435-45-5 nonadec-1-ene 
• 112-95-8 icosane 
• 629-97-0 n-docosane 
• 630-01-3 n-hexacosane 
• 593-45-3 octadecane 
• 646-31-1 tetracosane 

Downstream Products

• 506-50-3 melissic acid 
• 120727-03-9 trans-triacontyl-4-hydroxycinnamate 
• 4209-22-7 n-Triacontyl bromide 
• 22725-63-9 1-triacosanal 
• 6027-71-0 triacontyl hexadecanoate 
• 41755-58-2 n-triacontyl acetate 

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