544-64-9

Basic information

• Product Name: MYRISTOLEIC ACID
• Synonyms: MYRISTOLEIC ACID;DELTA 9 CIS TETRADECENOIC ACID;CIS-9-TETRADECENOIC ACID;C14:1 (CIS-9) ACID;(z)-9-tetradecenoicaci;(Z)-9-Tetradecenoicacid;(Z)-tetradec-9-enoic acid;MYRISTOLEIC ACID 99%
• CAS NO: 544-64-9
• Molecular Formula: C₁₄H₂₆O₂
• Molecular Weight: 226.36
• EINECS: 208-876-8
• Mol File: 544-64-9.mol
• Article Data: 5

Chemical Properties

• Melting Point: −4.5-−4 °C(lit.)
• Boiling Point: 144 °C0.6 mm Hg(lit.)
• Flash Point: 62 °C
• Appearance: /Liquid
• Density: 0.9 g/mL at 25 °C(lit.)
• Vapor Pressure: 1.77E-05mmHg at 25°C
• Refractive Index: n20/D 1.4562(lit.)
• Storage Temp.: −20°C
• Solubility: Benzene (Slightly), Chloroform (Slightly), Methanol (Slightly)
• PKA: 4.78±0.10(Predicted)
• CAS DataBase Reference: MYRISTOLEIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: MYRISTOLEIC ACID(544-64-9)
• EPA Substance Registry System: MYRISTOLEIC ACID(544-64-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• RIDADR: NA 1993 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 544-64-9(Hazardous Substances Data)

Usage

Description

Myristoleic Acid, a colorless liquid, is a naturally occurring monounsaturated fatty acid found in the fat of some seeds and fish oil. It possesses unique chemical properties that make it a promising compound for various applications, particularly in the medical field.

Uses

Used in Pharmaceutical Industry:
Myristoleic Acid is used as a therapeutic agent for the treatment of prostate cancer. It induces apoptosis and necrosis in human prostate cancer cell LNCaP, demonstrating its potential as a new tool in developing treatments for prostate cancer.
Used in Nutritional Supplements:
Myristoleic Acid, being a naturally occurring fatty acid, can be used as a component in nutritional supplements to support overall health and well-being. Its presence in fish oil and some seeds makes it a valuable addition to dietary supplements for those seeking a natural source of essential fatty acids.
Used in Research and Development:
Due to its unique chemical properties and potential applications in the medical field, Myristoleic Acid can be utilized in research and development for the discovery of new drugs and therapies. Its role in inducing apoptosis and necrosis in cancer cells makes it an interesting subject for further study and potential development of novel cancer treatments.

InChI:InChI=1/C14H26O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14(15)16/h5-6H,2-4,7-13H2,1H3,(H,15,16)/b6-5-

Synthetic route

cis-9-cetyl myristoleate (64660-84-0) → myristoleic acid (544-64-9) + 1-Hexadecanol (36653-82-4)

Conditions	Yield
With sodium hydroxide In water; acetone for 14h; Heating;	A 80% B 50%

myristoleic acid ethyl ester (24880-50-0) → myristoleic acid (544-64-9)

Conditions	Yield
With sodium hydroxide
With sodium hydroxide In methanol
With water; sodium hydroxide at 20℃; for 3h;

9-tetradecynoic acid (55182-92-8) → myristoleic acid (544-64-9)

Conditions	Yield
With quinoline; hydrogen; palladium on barium sulfate In methanol

(Z)-9-tetradecen-1-ol (35153-15-2) → myristoleic acid (544-64-9)

Conditions	Yield
With dipyridinium dichromate In N,N-dimethyl-formamide at 25℃; for 12h; Oxidation;

8-bromooctanoic acid (17696-11-6) → myristoleic acid (544-64-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: (i) LiNH2, liq. NH3, (ii) /BRN= 1756103/, THF 2: H2, quinoline / Pd-BaSO4 / methanol View Scheme
Multi-step reaction with 5 steps 1: acetyl chloride / 4 h / 20 °C 2: 18 h / 20 °C 3: sodium phosphinate / 2 h / 40 °C 4: sodium hexamethyldisilazane / tetrahydrofuran / 2 h / -78 - 20 °C 5: sodium hydroxide; water / 3 h / 20 °C View Scheme

hex-1-yne (693-02-7) + tertiary amine → myristoleic acid (544-64-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: (i) LiNH2, liq. NH3, (ii) /BRN= 1756103/, THF 2: H2, quinoline / Pd-BaSO4 / methanol View Scheme

oleic acid ethyl ester (111-62-6) + ClSO3Na → myristoleic acid (544-64-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: (i) O3, CH2Cl2, (ii) Ph3P 2: (i) K, HMPT, (ii) /BRN= 1769505/ 3: aq. NaOH / methanol View Scheme

ethyl 9-oxononanoate (3433-16-7) → myristoleic acid (544-64-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: (i) K, HMPT, (ii) /BRN= 1769505/ 2: aq. NaOH / methanol View Scheme
Multi-step reaction with 2 steps 1: sodium hexamethyldisilazane / tetrahydrofuran / 2 h / -78 - 20 °C 2: sodium hydroxide; water / 3 h / 20 °C View Scheme

ethyl 8-cyanooctanoate → myristoleic acid (544-64-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium phosphinate / 2 h / 40 °C 2: sodium hexamethyldisilazane / tetrahydrofuran / 2 h / -78 - 20 °C 3: sodium hydroxide; water / 3 h / 20 °C View Scheme

Ethyl 8-bromooctanoate (29823-21-0) → myristoleic acid (544-64-9)

Conditions	Yield
Multi-step reaction with 4 steps 1: 18 h / 20 °C 2: sodium phosphinate / 2 h / 40 °C 3: sodium hexamethyldisilazane / tetrahydrofuran / 2 h / -78 - 20 °C 4: sodium hydroxide; water / 3 h / 20 °C View Scheme

myristoleic acid (544-64-9) → 10-hydroxytetradecanoic acid (16899-08-4)

Conditions	Yield
With recombinant Chryseobacterium gleum oleate hydratase In aq. phosphate buffer at 25℃; for 21h; pH=6.5; Catalytic behavior; Reagent/catalyst;	95%
With oleate hydratase from macrococcus caseolyticus; water; flavin adenine dinucleotide In ethanol at 25℃; for 0.166667h; pH=6.5; PIPES buffer; Enzymatic reaction;

myristoleic acid (544-64-9) + di-tert-butyl butane-1,4-diylbis((3-aminopropyl)carbamate) (177213-61-5) → N1,N12-dimyristoleoyl-N4,N9-di(t-butoxycarbonyl)-1,12-diamino-4,9-diazadodecane (1202704-85-5)

Conditions	Yield
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 16h;	76%

myristoleic acid (544-64-9) + glycine ethyl ester hydrochloride (623-33-6) → ethyl 2-[[(Z)-tetradec-9-enoyl]amino]acetate

Conditions	Yield
Stage #1: myristoleic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: glycine ethyl ester hydrochloride With triethylamine In N,N-dimethyl-formamide for 18h;	70%

myristoleic acid (544-64-9) + 3-O-[2,3,4-tri-O-(tert-butyldimethylsilyl)-6-deoxy-6-thioacetyl-α-D-glucopyranosyl]-glycerol (265312-96-7) → 3-O-[2,3,4-tri-O-(tert-butyldimethylsilyl)-6-deoxy-6-thioacetyl-α-D-glucopyranosyl]-1-O-myristoleoyl-glycerol (338745-56-5)

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 6h; esterification;	60.9%

diiodomethane (75-11-6) + myristoleic acid (544-64-9) → cis-9,10-methylenetetradecanoic acid

Conditions	Yield
Stage #1: diiodomethane With diethylzinc; 2,4,6-Trichlorophenol In hexane; dichloromethane at -40℃; for 0.25h; Inert atmosphere; Stage #2: myristoleic acid In hexane; dichloromethane at -40 - 20℃; Inert atmosphere;	39%

myristoleic acid (544-64-9) + di-tert-butyl (2R)-2,3-dihydroxypropyl phosphate → (2R)-3-[(di-tert-butoxyphosphoryl)oxy]-2-hydroxypropyl (9Z)-tetradec-9-enoate

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at -20 - 20℃; for 16h; Inert atmosphere; regioselective reaction;	28%

myristoleic acid (544-64-9) + methyllithium (917-54-4) → pentadec-10c-en-2-one (58257-60-6)

myristoleic acid (544-64-9) → (+/-)-threo-9.10-dihydroxy-myristic acid (1747-02-0, 127082-58-0)

Conditions	Yield
With formic acid; dihydrogen peroxide at 40℃; for 2h;

myristoleic acid (544-64-9) + 1-Hexadecanol (36653-82-4) → cis-9-cetyl myristoleate (64660-84-0)

Conditions	Yield
With toluene-4-sulfonic acid In benzene for 4h; Heating;	300 mg

myristoleic acid (544-64-9) → myristoleoyl chloride

Conditions	Yield
With oxalyl dichloride for 3h;
With oxalyl dichloride In benzene at 20℃; for 2h; Inert atmosphere;

myristoleic acid (544-64-9) + (2R,3R)-5,7-bis((tert-butyldimethylsilyl)oxy)-2-(3,4,5-tris((tert-butyldimethylsilyl)oxy)phenyl)chroman-3-ol → tetradec-9-enoic acid 5,7-bis-(tert-butyl-dimethyl-silanyloxy)-2-[3,4,5-tris-(tert-butyl-dimethyl-silanyloxy)-phenyl]-chroman-3-yl ester

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide

(S)-2-{(S)-2-[(S)-2-((S)-2-{[(2S,4S)-1-(2-tert-Butoxycarbonylamino-2-methyl-propionyl)-4-hydroxy-pyrrolidine-2-carbonyl]-amino}-4-methyl-pentanoylamino)-3-methyl-butyrylamino]-4-carbamoyl-butyrylamino}-4-methyl-pentanoic acid methyl ester + myristoleic acid (544-64-9) → (S)-2-((S)-4-Carbamoyl-2-{(S)-2-[(S)-2-({(2S,4S)-4-hydroxy-1-[2-methyl-2-((Z)-tetradec-9-enoylamino)-propionyl]-pyrrolidine-2-carbonyl}-amino)-4-methyl-pentanoylamino]-3-methyl-butyrylamino}-butyrylamino)-4-methyl-pentanoic acid methyl ester

Conditions

Yield

Stage #1: (S)-2-{(S)-2-[(S)-2-((S)-2-{[(2S,4S)-1-(2-tert-Butoxycarbonylamino-2-methyl-propionyl)-4-hydroxy-pyrrolidine-2-carbonyl]-amino}-4-methyl-pentanoylamino)-3-methyl-butyrylamino]-4-carbamoyl-butyrylamino}-4-methyl-pentanoic acid methyl ester With trifluoroacetic acid at 20℃; for 0.333333h; Stage #2: myristoleic acid With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;

10-carbon-sphingosine + myristoleic acid (544-64-9) → C24H45NO3

Conditions	Yield
Stage #1: myristoleic acid With dmap; diisopropyl-carbodiimide In 1-methyl-pyrrolidin-2-one at 20℃; Stage #2: 10-carbon-sphingosine In tetrahydrofuran at 20℃; Further stages.;

(2R,3S,4E)-2-aminododec-4-ene-1,3-diol + myristoleic acid (544-64-9) → C26H49NO3

Conditions	Yield
Stage #1: myristoleic acid With dmap; diisopropyl-carbodiimide In 1-methyl-pyrrolidin-2-one at 20℃; Stage #2: (2R,3S,4E)-2-aminododec-4-ene-1,3-diol In tetrahydrofuran at 20℃; Further stages.;

15-carbon-sphingosine + myristoleic acid (544-64-9) → C29H55NO3

Conditions	Yield
Stage #1: myristoleic acid With dmap; diisopropyl-carbodiimide In 1-methyl-pyrrolidin-2-one at 20℃; Stage #2: 15-carbon-sphingosine In tetrahydrofuran at 20℃; Further stages.;

myristoleic acid (544-64-9) + (2S,3R,4E)-2-amino-4-octadecene-1,3-diol (123-78-4) → C32H61NO3

Conditions	Yield
Stage #1: myristoleic acid With dmap; diisopropyl-carbodiimide In 1-methyl-pyrrolidin-2-one at 20℃; Stage #2: (2S,3R,4E)-2-amino-4-octadecene-1,3-diol In tetrahydrofuran at 20℃; Further stages.;

20-carbon-sphingosine + myristoleic acid (544-64-9) → C34H65NO3

Conditions	Yield
Stage #1: myristoleic acid With dmap; diisopropyl-carbodiimide In 1-methyl-pyrrolidin-2-one at 20℃; Stage #2: 20-carbon-sphingosine In tetrahydrofuran at 20℃; Further stages.;

myristoleic acid (544-64-9) + (2R,3S,4E)-2-aminooctadec-4-ene-1,3-diol (6036-75-5) → C32H61NO3

Conditions	Yield
Stage #1: myristoleic acid With dmap; diisopropyl-carbodiimide In 1-methyl-pyrrolidin-2-one at 20℃; Stage #2: (2R,3S,4E)-2-aminooctadec-4-ene-1,3-diol In tetrahydrofuran at 20℃; Further stages.;

myristoleic acid (544-64-9) + (2R,3R,4E)-2-amino-octadec-4-ene-1,3-diol (6036-85-7) → C32H61NO3

Conditions	Yield
Stage #1: myristoleic acid With dmap; diisopropyl-carbodiimide In 1-methyl-pyrrolidin-2-one at 20℃; Stage #2: (2R,3R,4E)-2-amino-octadec-4-ene-1,3-diol In tetrahydrofuran at 20℃; Further stages.;

myristoleic acid (544-64-9) + (2S,3S,4E)-L-threo sphingosine (25695-95-8) → C32H61NO3

Conditions	Yield
Stage #1: myristoleic acid With dmap; diisopropyl-carbodiimide In 1-methyl-pyrrolidin-2-one at 20℃; Stage #2: (2S,3S,4E)-L-threo sphingosine In tetrahydrofuran at 20℃; Further stages.;

dihydrosphingosine (3102-56-5) + myristoleic acid (544-64-9) → C32H63NO3

Conditions	Yield
Stage #1: myristoleic acid With dmap; diisopropyl-carbodiimide In 1-methyl-pyrrolidin-2-one at 20℃; Stage #2: dihydrosphingosine In tetrahydrofuran at 20℃; Further stages.;

(+/-)-threo-dihydro-sphingosine (764-22-7, 2304-75-8, 3102-56-5, 3102-60-1, 6036-76-6, 6036-86-8, 13552-09-5, 15639-50-6, 73938-69-9) + myristoleic acid (544-64-9) → C32H63NO3

Conditions	Yield
Stage #1: myristoleic acid With dmap; diisopropyl-carbodiimide In 1-methyl-pyrrolidin-2-one at 20℃; Stage #2: (+/-)-threo-dihydro-sphingosine In tetrahydrofuran at 20℃; Further stages.;

(2S,3R)-2-amino-1,3-octadecanediol (764-22-7, 2304-75-8, 3102-56-5, 3102-60-1, 6036-76-6, 6036-86-8, 13552-09-5, 15639-50-6, 73938-69-9) + myristoleic acid (544-64-9) → C32H63NO3

Conditions	Yield
Stage #1: myristoleic acid With dmap; diisopropyl-carbodiimide In 1-methyl-pyrrolidin-2-one at 20℃; Stage #2: (2S,3R)-2-amino-1,3-octadecanediol In tetrahydrofuran at 20℃; Further stages.;

myristoleic acid (544-64-9) + (1S,2R)-(+)-norphedrine (37577-28-9) → C23H37NO2

Conditions	Yield
Stage #1: myristoleic acid With dmap; diisopropyl-carbodiimide In 1-methyl-pyrrolidin-2-one at 20℃; Stage #2: (1S,2R)-(+)-norphedrine In tetrahydrofuran at 20℃; Further stages.;

Upstream product

• 24880-50-0 myristoleic acid ethyl ester 
• 35153-15-2 (Z)-9-tetradecen-1-ol 
• 693-02-7 hex-1-yne 
• 29823-21-0 Ethyl 8-bromooctanoate 
• 3433-16-7 ethyl 9-oxononanoate 
• 111-62-6 oleic acid ethyl ester 
• 17696-11-6 8-bromooctanoic acid 
• 64660-84-0 cis-9-cetyl myristoleate 
• 55182-92-8 9-tetradecynoic acid 

Downstream Products

• 64660-84-0 cis-9-cetyl myristoleate 
• 150989-01-8 myristoleoyl chloride 
• 100303-39-7 Z-9-Tetradecenoyl fluoride 
• 40853-87-0 (Z)-9-tetradecenylamine 
• 16899-08-4 10-hydroxytetradecanoic acid 
• 848441-65-6 Z-tetradec-9-enoic acid [3-(2-diethylamino-acetylamino)-2,4-dimethyl-phenyl]-amide 

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