Product Name

  • Name

    3-HYDROXYTETRADECANOIC ACID

  • EINECS
  • CAS No. 28715-21-1
  • Article Data26
  • CAS DataBase
  • Density 0.969g/cm3
  • Solubility
  • Melting Point 71-72°C
  • Formula C14H28 O3
  • Boiling Point 376.9°C at 760 mmHg
  • Molecular Weight 244.375
  • Flash Point 195.9°C
  • Transport Information
  • Appearance White Powder
  • Safety
    WGK Germany 3
  • Risk Codes
  • Molecular Structure Molecular Structure of 28715-21-1 (3-HYDROXYTETRADECANOIC ACID)
  • Hazard Symbols
  • Synonyms Tetradecanoicacid, 3-hydroxy-, (R)-; Tetradecanoic acid, 3-hydroxy-, D-(-)- (8CI);(3R)-3-Hydroxytetradecanoic acid; (R)-(-)-3-Hydroxytetradecanoic acid;(R)-3-Hydroxymyristic acid; (R)-3-Hydroxytetradecanoic acid; D-(-)-b-Hydroxymyristic acid;D-3-Hydroxytetradecanoic acid
  • PSA 57.53000
  • LogP 3.74290

Synthetic route

methyl 3-oxotetradecanoate
22348-97-6

methyl 3-oxotetradecanoate

(R)-3-hydroxytetradecanoic acid
28715-21-1

(R)-3-hydroxytetradecanoic acid

Conditions
ConditionsYield
Stage #1: methyl 3-oxotetradecanoate With hydrogen; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl; ruthenium trichloride In methanol at 40 - 50℃; under 3361.46 Torr; for 20h;
Stage #2: With lithium hydroxide In tetrahydrofuran; water
100%
With sodium hydroxide; hydrogen; acetic acid; L-Tartaric acid; (R,R)-tartaric acid-NaBr-Raney nickel ((R,R)-TA-NaBr-MRNi); sodium bromide 1.) C2H5COOCH3, 100 deg C, 100 kg/cm2; Yield given. Multistep reaction;
Multi-step reaction with 2 steps
1: 95.6 percent / H2 / (R)-ruthenium 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl / methanol / 5 h / 100 °C / 3750.3 Torr
2: 97.6 percent / lithium hydroxide monohydrate / methanol; H2O / 12 h
View Scheme
methyl (R)-3-hydroxytetradecanoate
76062-97-0

methyl (R)-3-hydroxytetradecanoate

(R)-3-hydroxytetradecanoic acid
28715-21-1

(R)-3-hydroxytetradecanoic acid

Conditions
ConditionsYield
With lithium hydroxide monohydrate In tetrahydrofuran; water at 20℃; for 2h;98%
With lithium hydroxide In methanol; water for 12h;97.6%
With sodium hydroxide In tetrahydrofuran; water Reflux;96%
(R)-1-cyanotridecan-2-ol
259799-90-1

(R)-1-cyanotridecan-2-ol

(R)-3-hydroxytetradecanoic acid
28715-21-1

(R)-3-hydroxytetradecanoic acid

Conditions
ConditionsYield
With hydrogenchloride In dichloromethane at 100℃; for 12h; Hydrolysis;95%
(R)-tert-butyl 3-hydroxytetradecanoate
79816-65-2

(R)-tert-butyl 3-hydroxytetradecanoate

(R)-3-hydroxytetradecanoic acid
28715-21-1

(R)-3-hydroxytetradecanoic acid

Conditions
ConditionsYield
With triethylsilane; trifluoroacetic acid In dichloromethane at 20℃; for 0.75h;87%
(R)-3-hydroxytetradecanoic acid ethyl ester
151763-75-6

(R)-3-hydroxytetradecanoic acid ethyl ester

(R)-3-hydroxytetradecanoic acid
28715-21-1

(R)-3-hydroxytetradecanoic acid

Conditions
ConditionsYield
With potassium hydroxide In ethanol76%
With ethanol; potassium hydroxide
3-hydroxytetradecanoic acid
1961-72-4

3-hydroxytetradecanoic acid

(R)-3-hydroxytetradecanoic acid
28715-21-1

(R)-3-hydroxytetradecanoic acid

Conditions
ConditionsYield
With dexamfetamine
Ethyl 3-hydroxytetradecanoate
126679-29-6

Ethyl 3-hydroxytetradecanoate

(R)-3-hydroxytetradecanoic acid
28715-21-1

(R)-3-hydroxytetradecanoic acid

Conditions
ConditionsYield
In diethyl ether (saponification);
vinyl acetate
108-05-4

vinyl acetate

3-hydroxytetradecanoic acid
1961-72-4

3-hydroxytetradecanoic acid

A

(R)-3-hydroxytetradecanoic acid
28715-21-1

(R)-3-hydroxytetradecanoic acid

B

(S)-3-acetoxytetradecanoic acid
151378-83-5

(S)-3-acetoxytetradecanoic acid

Conditions
ConditionsYield
With di-tert-butyl-4-methylphenol In tetrahydrofuran at 65℃; for 3h; Pseudomonas lipase;
3-oxomyristic acid
88222-72-4

3-oxomyristic acid

A

(R)-3-hydroxytetradecanoic acid
28715-21-1

(R)-3-hydroxytetradecanoic acid

B

tridecan-2-one
593-08-8

tridecan-2-one

Conditions
ConditionsYield
With potassium dihydrogenphosphate; baker's yeast; D-glucose In water at 28℃; for 48h; Yield given. Yields of byproduct given;
(3R)-1-trimethylsilyl-tetradec-1-yn-3-ol
74794-26-6

(3R)-1-trimethylsilyl-tetradec-1-yn-3-ol

A

(R)-3-hydroxytetradecanoic acid
28715-21-1

(R)-3-hydroxytetradecanoic acid

B

(3S)-3-hydroxytetradecanoic acid
35683-15-9

(3S)-3-hydroxytetradecanoic acid

Conditions
ConditionsYield
With sodium hydroxide; bis(cyclohexanyl)borane; dihydrogen peroxide 1) THF, 0 deg C; 2) 40-50 deg C; Yield given. Multistep reaction. Title compound not separated from byproducts;
n-dodecanoyl chloride
112-16-3

n-dodecanoyl chloride

(R)-3-hydroxytetradecanoic acid
28715-21-1

(R)-3-hydroxytetradecanoic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: pyridine / CH2Cl2 / 3 h / 0 - 20 °C
1.2: 77.9 percent / methanol / 3 h / Heating
2.1: 95.6 percent / H2 / (R)-ruthenium 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl / methanol / 5 h / 100 °C / 3750.3 Torr
3.1: 97.6 percent / lithium hydroxide monohydrate / methanol; H2O / 12 h
View Scheme
1-tridecene
2437-56-1

1-tridecene

(R)-3-hydroxytetradecanoic acid
28715-21-1

(R)-3-hydroxytetradecanoic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: K3Fe(CN)6; K2CO3; water / 4,6-bis(9-O-dihydroquinidinyl)-2,5-diphenylpyrimidine; OsO4 / 2-methyl-propan-2-ol; toluene / 24 h / 20 °C
2: 92 percent / pyridine; thionyl chloride / 5 h / 0 °C
3: 86 percent / dimethylformamide / 12 h / 90 °C
4: 95 percent / aq. HCl / CH2Cl2 / 12 h / 100 °C
View Scheme
(R)-1,2-dihydroxytridecane
96883-16-8

(R)-1,2-dihydroxytridecane

(R)-3-hydroxytetradecanoic acid
28715-21-1

(R)-3-hydroxytetradecanoic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 92 percent / pyridine; thionyl chloride / 5 h / 0 °C
2: 86 percent / dimethylformamide / 12 h / 90 °C
3: 95 percent / aq. HCl / CH2Cl2 / 12 h / 100 °C
View Scheme
(4R)-4-undecyl-1,3,2-dioxathiolane-2-oxide
259799-88-7

(4R)-4-undecyl-1,3,2-dioxathiolane-2-oxide

(R)-3-hydroxytetradecanoic acid
28715-21-1

(R)-3-hydroxytetradecanoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 86 percent / dimethylformamide / 12 h / 90 °C
2: 95 percent / aq. HCl / CH2Cl2 / 12 h / 100 °C
View Scheme
n-decyl magnesium bromide
17049-50-2

n-decyl magnesium bromide

HgBr2

HgBr2

(R)-3-hydroxytetradecanoic acid
28715-21-1

(R)-3-hydroxytetradecanoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1.) CuI / 1.) THF, -30 deg C, 30 min, 2.) THF, a) -30 deg C, 1 h, b) RT, overnight
2: 76 percent / aq. KOH / ethanol
View Scheme
n-dodecanoyl chloride
112-16-3

n-dodecanoyl chloride

alcoholic NaOH

alcoholic NaOH

(R)-3-hydroxytetradecanoic acid
28715-21-1

(R)-3-hydroxytetradecanoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
2: di-t-butyl-p-cresol / tetrahydrofuran / 3 h / 65 °C / Pseudomonas lipase
View Scheme
2,2-dimethyl-4,6-dioxo-5-dodecanoyl-1,3-dioxane
111861-21-3

2,2-dimethyl-4,6-dioxo-5-dodecanoyl-1,3-dioxane

(R)-3-hydroxytetradecanoic acid
28715-21-1

(R)-3-hydroxytetradecanoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: methanol / 5 h / Heating
2: 1.) H2, AcOH, 2.) NaOH / 1.) (R,R)-tartaric acid-NaBr-Raney nickel ((R,R)-TA-NaBr-MRNi) / 1.) C2H5COOCH3, 100 deg C, 100 kg/cm2
View Scheme
(R)-(-)-1-tetradecyn-3-ol
77889-04-4, 136022-04-3, 73501-38-9

(R)-(-)-1-tetradecyn-3-ol

(R)-3-hydroxytetradecanoic acid
28715-21-1

(R)-3-hydroxytetradecanoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1) 2.4 eq. n-BuLi; 2) 1.4 M H2SO4 / 1) THF, -78 deg C; 2) from -20 deg C to room temperature
2: 1) 2 eq. dicyclohexylborane; 2) NaOH, H2O2 / 1) THF, 0 deg C; 2) 40-50 deg C
View Scheme
tetradec-1-yn-3-one
73501-40-3

tetradec-1-yn-3-one

(R)-3-hydroxytetradecanoic acid
28715-21-1

(R)-3-hydroxytetradecanoic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1.4 eq. R-Alpine-Borane / neat (no solvent) / 8 h / 0 - 20 °C
2: 1) 2.4 eq. n-BuLi; 2) 1.4 M H2SO4 / 1) THF, -78 deg C; 2) from -20 deg C to room temperature
3: 1) 2 eq. dicyclohexylborane; 2) NaOH, H2O2 / 1) THF, 0 deg C; 2) 40-50 deg C
View Scheme
1,4-dioxane
123-91-1

1,4-dioxane

methyl (R)-3-hydroxytetradecanoate
76062-97-0

methyl (R)-3-hydroxytetradecanoate

(R)-3-hydroxytetradecanoic acid
28715-21-1

(R)-3-hydroxytetradecanoic acid

Conditions
ConditionsYield
With hydrogenchloride; sodium hydroxide In methanol; water
n-tetradecanoic acid
544-63-8

n-tetradecanoic acid

A

2-hydroxytetradecanoic acid
2507-55-3

2-hydroxytetradecanoic acid

B

(R)-3-hydroxytetradecanoic acid
28715-21-1

(R)-3-hydroxytetradecanoic acid

Conditions
ConditionsYield
With recombinant Bacillus subtilis cytochrome P450(BSβ) F79L mutant; dihydrogen peroxide at 37℃; for 0.0166667h; pH=7; Kinetics; Concentration; Reagent/catalyst; aq. phosphate buffer; Enzymatic reaction; regioselective reaction;
jagaricin
1422729-34-7

jagaricin

A

D-allo-threonine
24830-94-2

D-allo-threonine

B

(2S,3S)-2-amino-3-hydroxybutanoic acid
28954-12-3

(2S,3S)-2-amino-3-hydroxybutanoic acid

C

L-threonine
72-19-5

L-threonine

D

D-Glutamin
5959-95-5

D-Glutamin

E

(R)-3-hydroxytetradecanoic acid
28715-21-1

(R)-3-hydroxytetradecanoic acid

F

dehydrobutyrine
20748-08-7

dehydrobutyrine

G

tyrosine
556-02-5

tyrosine

H

glycine
56-40-6

glycine

I

L-histidine
71-00-1

L-histidine

Conditions
ConditionsYield
With hydrogenchloride; phenol In water at 105℃; Reagent/catalyst;
(+/-)-3-hydroxytetradecanoic acid methyl ester
55682-83-2

(+/-)-3-hydroxytetradecanoic acid methyl ester

A

(R)-3-hydroxytetradecanoic acid
28715-21-1

(R)-3-hydroxytetradecanoic acid

B

(S)-methyl 3-hydroxymyristate
76835-67-1

(S)-methyl 3-hydroxymyristate

Conditions
ConditionsYield
With Porcine Pancreas Lipase; water In aq. phosphate buffer at 36℃; for 7h; pH=7.6; enantioselective reaction;A n/a
B n/a
With Porcine Pancreas Lipase; water In aq. phosphate buffer at 36℃; for 7h; pH=7.6; Resolution of racemate; enantioselective reaction;A n/a
B n/a
(+/-)-3-hydroxytetradecanoic acid methyl ester
55682-83-2

(+/-)-3-hydroxytetradecanoic acid methyl ester

A

(R)-3-hydroxytetradecanoic acid
28715-21-1

(R)-3-hydroxytetradecanoic acid

B

(S)-methyl 3-hydroxymyristate
76835-67-1

(S)-methyl 3-hydroxymyristate

C

(3S)-3-hydroxytetradecanoic acid
35683-15-9

(3S)-3-hydroxytetradecanoic acid

Conditions
ConditionsYield
With Porcine Pancreas Lipase; water In aq. phosphate buffer at 36℃; for 7h; pH=7.6; Resolution of racemate; enantioselective reaction;A n/a
B n/a
C n/a
lauric acid
143-07-7

lauric acid

(R)-3-hydroxytetradecanoic acid
28715-21-1

(R)-3-hydroxytetradecanoic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: magnesium ethylate / 1,4-dioxane
1.2: 20 °C
2.1: hydrogen; dichloro-R-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl ruthenium / methanol / 20 h / 50 °C / 3102.97 Torr / Inert atmosphere
3.1: lithium hydroxide monohydrate / water; tetrahydrofuran / 2 h / 20 °C
View Scheme
C37H66N4O8

C37H66N4O8

A

L-leucine
61-90-5

L-leucine

B

L-glutamic acid
56-86-0

L-glutamic acid

C

(R)-3-hydroxytetradecanoic acid
28715-21-1

(R)-3-hydroxytetradecanoic acid

Conditions
ConditionsYield
With hydrogenchloride In water at 123℃; for 23h;
1-hydroxy-pyrrolidine-2,5-dione
6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

(R)-3-hydroxytetradecanoic acid
28715-21-1

(R)-3-hydroxytetradecanoic acid

N-<(R)-3-hydroxytetradecanoyloxy>succinimide

N-<(R)-3-hydroxytetradecanoyloxy>succinimide

Conditions
ConditionsYield
With 2`,3`-dideoxycytidine In tetrahydrofuran for 12h; Ambient temperature;100%
methanol
67-56-1

methanol

(R)-3-hydroxytetradecanoic acid
28715-21-1

(R)-3-hydroxytetradecanoic acid

methyl (R)-3-hydroxytetradecanoate
76062-97-0

methyl (R)-3-hydroxytetradecanoate

Conditions
ConditionsYield
With boron trifluoride at 100℃; for 0.0333333h;100%
With boron trifluoride at 105℃; for 0.75h;
(R)-3-hydroxytetradecanoic acid
28715-21-1

(R)-3-hydroxytetradecanoic acid

α-bromoacetophenone
70-11-1

α-bromoacetophenone

(3R)-3-hydroxytetradecanoic acid phenacyl ester
87357-65-1

(3R)-3-hydroxytetradecanoic acid phenacyl ester

Conditions
ConditionsYield
With triethylamine In ethyl acetate98%
With triethylamine In ethyl acetate 1.) 0 deg C, 10 min, 2.) room temp.;94%
With triethylamine In ethyl acetate93%
(R)-3-hydroxytetradecanoic acid
28715-21-1

(R)-3-hydroxytetradecanoic acid

benzyl chloride
100-44-7

benzyl chloride

3-hydroxy-D-tetradecanoic acid benzyl ester
88862-84-4

3-hydroxy-D-tetradecanoic acid benzyl ester

Conditions
ConditionsYield
In tetrahydrofuran; dimethyl sulfoxide at 50℃;97%
(R)-3-hydroxytetradecanoic acid
28715-21-1

(R)-3-hydroxytetradecanoic acid

benzyl 2-amino-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside
102794-17-2

benzyl 2-amino-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside

benzyl 2-deoxy-2-<(3R)-3-hydroxytetradecanamido>-4,6-O-isopropylidene-β-D-glucopyranoside
104640-20-2

benzyl 2-deoxy-2-<(3R)-3-hydroxytetradecanamido>-4,6-O-isopropylidene-β-D-glucopyranoside

Conditions
ConditionsYield
With 3-{[(ethylimino)methylene]-amino}-N,N,N-trimethyl-1-propanaminium iodide In dichloromethane95%
With dicyclohexyl-carbodiimide In dichloromethane for 3h; Ambient temperature; Yield given;
(R)-3-hydroxytetradecanoic acid
28715-21-1

(R)-3-hydroxytetradecanoic acid

{(2R,3R,4S,5S,6S)-6-[(2R,3S,4R,5R,6S)-5-Amino-6-((2R,3S,4R,5R,6R)-5-amino-3,4-bis-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-4-benzyloxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy]-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yl}-methanol
96961-24-9

{(2R,3R,4S,5S,6S)-6-[(2R,3S,4R,5R,6S)-5-Amino-6-((2R,3S,4R,5R,6R)-5-amino-3,4-bis-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-4-benzyloxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy]-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yl}-methanol

C89H124N2O18
96961-25-0

C89H124N2O18

Conditions
ConditionsYield
With N-ethylmorpholine;; benzotriazol-1-ol; dicyclohexyl-carbodiimide In 1,4-dioxane at 20℃; for 2h;88%
(R)-3-hydroxytetradecanoic acid
28715-21-1

(R)-3-hydroxytetradecanoic acid

triethylsilyl chloride
994-30-9

triethylsilyl chloride

(R)-3-O-triethylsilyl myristic acid
915406-25-6

(R)-3-O-triethylsilyl myristic acid

Conditions
ConditionsYield
In pyridine at 60℃; for 2h;85.6%
(R)-3-hydroxytetradecanoic acid
28715-21-1

(R)-3-hydroxytetradecanoic acid

2-(trimethylsilyl)ethyl 2-amino-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside
122078-72-2

2-(trimethylsilyl)ethyl 2-amino-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside

2-(trimethylsilyl)ethyl 2-deoxy-2-<(3R)-3-hydroxytetradecanamido>-4,6-O-isopropylidene-β-D-glucopyranoside
122078-73-3

2-(trimethylsilyl)ethyl 2-deoxy-2-<(3R)-3-hydroxytetradecanamido>-4,6-O-isopropylidene-β-D-glucopyranoside

Conditions
ConditionsYield
With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane Ambient temperature;84%
1-hydroxy-pyrrolidine-2,5-dione
6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

(R)-3-hydroxytetradecanoic acid
28715-21-1

(R)-3-hydroxytetradecanoic acid

N-(R)-3-hydroxytetradecanoyloxysuccinimide
33796-65-5

N-(R)-3-hydroxytetradecanoyloxysuccinimide

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In ethyl acetate at 0℃; for 16h;80%
1H-imidazole
288-32-4

1H-imidazole

(R)-3-hydroxytetradecanoic acid
28715-21-1

(R)-3-hydroxytetradecanoic acid

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

(R)-3-t-Butyldimethyl-Silyloxytetradecanoic Acid

(R)-3-t-Butyldimethyl-Silyloxytetradecanoic Acid

Conditions
ConditionsYield
In methanol; dichloromethane; chloroform79%
(R)-3-hydroxytetradecanoic acid
28715-21-1

(R)-3-hydroxytetradecanoic acid

(R)-1,3-dihydroxytetradecane
139623-13-5

(R)-1,3-dihydroxytetradecane

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran for 2.5h; Ambient temperature;76%
(R)-3-hydroxytetradecanoic acid
28715-21-1

(R)-3-hydroxytetradecanoic acid

1,3,4,6-tetra-O-acetyl-D-glucosamine hydrochloride
5432-46-2, 10034-19-2, 10034-20-5, 34948-62-4, 110253-00-4

1,3,4,6-tetra-O-acetyl-D-glucosamine hydrochloride

1,3,4,6-tetra-O-acetyl-2-deoxy-<(3R)-3-hydroxytetradecanamido>-β-D-glucopyranose
74660-52-9, 77448-50-1, 121700-61-6

1,3,4,6-tetra-O-acetyl-2-deoxy-<(3R)-3-hydroxytetradecanamido>-β-D-glucopyranose

Conditions
ConditionsYield
With triethylamine; dicyclohexyl-carbodiimide In pyridine for 48h; Ambient temperature;68%
(R)-3-hydroxytetradecanoic acid
28715-21-1

(R)-3-hydroxytetradecanoic acid

(S)-methyl 3-(tert-butoxy)-2-((R)-2-((tert-butoxycarbonyl)amino)-3-((2-hydroxyethyl)thio)propanamido)propanoate
1346422-43-2

(S)-methyl 3-(tert-butoxy)-2-((R)-2-((tert-butoxycarbonyl)amino)-3-((2-hydroxyethyl)thio)propanamido)propanoate

methyl (L-(thio-((R)-ethyl 3-hydroxytetradecanoate))-N-(tert-butoxycarbonyl))cysteyl-L-(3-O-(tert-butyl))serate
1620278-76-3

methyl (L-(thio-((R)-ethyl 3-hydroxytetradecanoate))-N-(tert-butoxycarbonyl))cysteyl-L-(3-O-(tert-butyl))serate

Conditions
ConditionsYield
With 4-methyl-morpholine; dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;63%
(R)-3-hydroxytetradecanoic acid
28715-21-1

(R)-3-hydroxytetradecanoic acid

benzyl bromide
100-39-0

benzyl bromide

3-hydroxy-D-tetradecanoic acid benzyl ester
88862-84-4

3-hydroxy-D-tetradecanoic acid benzyl ester

Conditions
ConditionsYield
With triethylamine In ethyl acetate for 72h; Ambient temperature;61%
With tetra-(n-butyl)ammonium iodide; triethylamine In ethyl acetate at 20℃; for 18h;
(R)-3-hydroxytetradecanoic acid
28715-21-1

(R)-3-hydroxytetradecanoic acid

Fmoc-Leu-OH
35661-60-0

Fmoc-Leu-OH

L-Asn(Trt)
132388-59-1

L-Asn(Trt)

Fmoc-L-Gln(Trt)-OH
132327-80-1

Fmoc-L-Gln(Trt)-OH

deoxy-fellutamide D

deoxy-fellutamide D

Conditions
ConditionsYield
Stage #1: Fmoc-Leu-OH With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃; for 6h; Weinreb amide resin;
Stage #2: With piperidine In N,N-dimethyl-formamide for 0.05h; Weinreb amide resin;
Stage #3: (R)-3-hydroxytetradecanoic acid; L-Asn(Trt); Fmoc-L-Gln(Trt)-OH Further stages;
60%
(R)-3-hydroxytetradecanoic acid
28715-21-1

(R)-3-hydroxytetradecanoic acid

Fmoc-Val-OH
68858-20-8

Fmoc-Val-OH

L-Asn(Trt)
132388-59-1

L-Asn(Trt)

Fmoc-L-Gln(Trt)-OH
132327-80-1

Fmoc-L-Gln(Trt)-OH

deoxy-fellutamide C

deoxy-fellutamide C

Conditions
ConditionsYield
Stage #1: Fmoc-Val-OH With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃; for 6h; Weinreb amide resin;
Stage #2: With piperidine In N,N-dimethyl-formamide for 0.05h; Weinreb amide resin;
Stage #3: (R)-3-hydroxytetradecanoic acid; L-Asn(Trt); Fmoc-L-Gln(Trt)-OH Further stages;
53%
(R)-3-hydroxytetradecanoic acid
28715-21-1

(R)-3-hydroxytetradecanoic acid

methyl (R)-3-hydroxytetradecanoate
76062-97-0

methyl (R)-3-hydroxytetradecanoate

Conditions
ConditionsYield
In diethyl ether Yield given;
methanol
67-56-1

methanol

(R)-3-hydroxytetradecanoic acid
28715-21-1

(R)-3-hydroxytetradecanoic acid

A

methyl (R)-3-hydroxytetradecanoate
76062-97-0

methyl (R)-3-hydroxytetradecanoate

B

(S)-methyl 3-hydroxymyristate
76835-67-1

(S)-methyl 3-hydroxymyristate

Conditions
ConditionsYield
With hydrogenchloride for 2h; Ambient temperature; Yield given. Title compound not separated from byproducts;
(R)-3-hydroxytetradecanoic acid
28715-21-1

(R)-3-hydroxytetradecanoic acid

Benzyl-6-O-<6-O-acetyl-2-amino-3-O-<α,α-D2>benzyl-2-desoxy-4-O-(diphenoxyphosphoryl)-β-D-glucopyranosyl>-2-amino-3,4-di-O-<α,α-D2>benzyl-2-desoxy-β-D-glucopyranosid-dihydrochlorid
106115-93-9

Benzyl-6-O-<6-O-acetyl-2-amino-3-O-<α,α-D2>benzyl-2-desoxy-4-O-(diphenoxyphosphoryl)-β-D-glucopyranosyl>-2-amino-3,4-di-O-<α,α-D2>benzyl-2-desoxy-β-D-glucopyranosid-dihydrochlorid

Benzyl-6-O-<6-O-acetyl-3-O-<α,α-D2>benzyl-2-desoxy-4-O-(diphenoxyphosphoryl)-2-<(R)-3-hydroxytetradecanoylamino>-β-D-glucopyranosyl>-3,4-di-O-<α,α-D2>benzyl-2-desoxy-2-<(R)-3-hydroxytetradecanoylamino>-β-D-glucopyranosid
106115-95-1

Benzyl-6-O-<6-O-acetyl-3-O-<α,α-D2>benzyl-2-desoxy-4-O-(diphenoxyphosphoryl)-2-<(R)-3-hydroxytetradecanoylamino>-β-D-glucopyranosyl>-3,4-di-O-<α,α-D2>benzyl-2-desoxy-2-<(R)-3-hydroxytetradecanoylamino>-β-D-glucopyranosid

Conditions
ConditionsYield
With cyclohexyl(2-morpholinoethyl)carbodiimide metho-p-toluenesulfonate; benzotriazol-1-ol; triethylamine 1.) DMF, 60 min, 2.) DMF, 1 h; Yield given. Multistep reaction;
(R)-3-hydroxytetradecanoic acid
28715-21-1

(R)-3-hydroxytetradecanoic acid

Benzyl-O-
106115-86-0

Benzyl-O-

C85H116(2)H6N2O24
106115-87-1

C85H116(2)H6N2O24

Conditions
ConditionsYield
With cyclohexyl-(2-morpholinoethyl)carbodiimide metho-p-toluenesulfonate; benzotriazol-1-ol; triethylamine 1.) DMF, 60 min, RT, 2.) DMF, 8 h, RT; Yield given. Multistep reaction;
(R)-3-hydroxytetradecanoic acid
28715-21-1

(R)-3-hydroxytetradecanoic acid

C34H34(2)H2NO9P*ClH
106139-09-7

C34H34(2)H2NO9P*ClH

Benzyl-6-O-acetyl-3-O-<α,α-D2>benzyl-2-desoxy-4-O-(diphenoxyphosphoryl)-2-<(R)-3-hydroxytetradecanoylamino>-β-D-glucopyranosid
106115-91-7

Benzyl-6-O-acetyl-3-O-<α,α-D2>benzyl-2-desoxy-4-O-(diphenoxyphosphoryl)-2-<(R)-3-hydroxytetradecanoylamino>-β-D-glucopyranosid

Conditions
ConditionsYield
With cyclohexyl(2-morpholinoethyl)carbodiimide metho-p-toluenesulfonate; benzotriazol-1-ol; triethylamine 1.) DMF, 60 min, 2.) DMF, 40 min, RT; Yield given. Multistep reaction;
(R)-3-hydroxytetradecanoic acid
28715-21-1

(R)-3-hydroxytetradecanoic acid

1,3-di-O-acetyl-2-amino-4,6-O-benzylidene-2-deoxy-β-D-glucopyranose hydrochloride
85065-28-7

1,3-di-O-acetyl-2-amino-4,6-O-benzylidene-2-deoxy-β-D-glucopyranose hydrochloride

Acetic acid (4aR,6S,7R,8R,8aS)-6-acetoxy-7-((R)-3-hydroxy-tetradecanoylamino)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester

Acetic acid (4aR,6S,7R,8R,8aS)-6-acetoxy-7-((R)-3-hydroxy-tetradecanoylamino)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester

Conditions
ConditionsYield
With triethylamine; dicyclohexyl-carbodiimide In pyridine
With triethylamine; dicyclohexyl-carbodiimide In pyridine

(R)-3-Hydroxymyristic acid Chemical Properties

Molecular Structure:

Molecular Formula: C14H28O3
Molecular Weight: 244.3703
Systematic Name: (3R)-3-Hydroxytetradecanoic acid
Synonyms of (R)-3-Hydroxymyristic acid (CAS NO.28715-21-1): (3R)-3-Hydroxytetradecanoic acid ; (R)-(-)-3-Hydroxytetradecanoic acid ; (R)-3-Hydroxytetradecanoic acid
CAS NO: 28715-21-1
Product Categories: Mixed Fatty Acids;Fatty Acid Derivatives & Lipids;Glycerols
Melting point: 71-72°C 
Index of Refraction: 1.467
Molar Refractivity: 69.96 cm3
Molar Volume: 252.1 cm3
Surface Tension: 37.7 dyne/cm
Density: 0.969 g/cm3
Flash Point: 195.9 °C
Enthalpy of Vaporization: 72.26 kJ/mol
Boiling Point: 376.9 °C at 760 mmHg
Vapour Pressure: 3.16E-07 mmHg at 25°C

(R)-3-Hydroxymyristic acid Uses

   (R)-3-Hydroxymyristic acid (CAS NO.28715-21-1) is used as one of two major component of bacterial Lipid A .

(R)-3-Hydroxymyristic acid Safety Profile

 WGK Germany of (R)-3-Hydroxymyristic acid (CAS NO.28715-21-1): 3

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