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28715-21-1

Basic Information
CAS No.: 28715-21-1
Name: 3-HYDROXYTETRADECANOIC ACID
Article Data: 26
Molecular Structure:
Molecular Structure of 28715-21-1 (3-HYDROXYTETRADECANOIC ACID)
Formula: C14H28 O3
Molecular Weight: 244.375
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
Density: 0.969g/cm3
Melting Point: 71-72°C
Boiling Point: 376.9°C at 760 mmHg
Flash Point: 195.9°C
Appearance: White Powder
Safety:
WGK Germany 3
PSA: 57.53000
LogP: 3.74290
Synthetic route
22348-97-6

methyl 3-oxotetradecanoate

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
76062-97-0

methyl (R)-3-hydroxytetradecanoate

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%
259799-90-1

(R)-1-cyanotridecan-2-ol

28715-21-1

(R)-3-hydroxytetradecanoic acid

Conditions
ConditionsYield
With hydrogenchloride In dichloromethane at 100℃; for 12h; Hydrolysis;95%
79816-65-2

(R)-tert-butyl 3-hydroxytetradecanoate

28715-21-1

(R)-3-hydroxytetradecanoic acid

Conditions
ConditionsYield
With triethylsilane; trifluoroacetic acid In dichloromethane at 20℃; for 0.75h;87%
151763-75-6

(R)-3-hydroxytetradecanoic acid ethyl ester

28715-21-1

(R)-3-hydroxytetradecanoic acid

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

3-hydroxytetradecanoic acid

28715-21-1

(R)-3-hydroxytetradecanoic acid

Conditions
ConditionsYield
With dexamfetamine
126679-29-6

Ethyl 3-hydroxytetradecanoate

28715-21-1

(R)-3-hydroxytetradecanoic acid

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

vinyl acetate

1961-72-4

3-hydroxytetradecanoic acid

A

28715-21-1

(R)-3-hydroxytetradecanoic acid

B

151378-83-5

(S)-3-acetoxytetradecanoic acid

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

3-oxomyristic acid

A

28715-21-1

(R)-3-hydroxytetradecanoic acid

B

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;
74794-26-6

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

A

28715-21-1

(R)-3-hydroxytetradecanoic acid

B

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;
Downstream Products
68711-40-0
139623-16-8
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Chemistry

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

Uses

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

Safety Profile

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