55682-83-2

Basic information

• Product Name: METHYL 3-HYDROXYTETRADECANOATE
• Synonyms: METHYL 3-HYDROXYTETRADECANOATE;3-HYDROXY C14:0 METHYL ESTER;Methyl (±)-3-hydroxymyristate;3-Hydroxytetradecanoic acid methyl ester;3-Hydroxy Myristic Acid Methyl Ester
• CAS NO: 55682-83-2
• Molecular Formula: C₁₅H₃₀O₃
• Molecular Weight: 258.4
• Product Categories: Fatty Acid Derivatives & Lipids;Glycerols
• Mol File: 55682-83-2.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 359.1°Cat760mmHg
• Flash Point: 137.5°C
• Appearance: /
• Density: 0.931g/cm³
• Vapor Pressure: 1.33E-06mmHg at 25°C
• Refractive Index: 1.451
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 13.91±0.20(Predicted)
• CAS DataBase Reference: METHYL 3-HYDROXYTETRADECANOATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL 3-HYDROXYTETRADECANOATE(55682-83-2)
• EPA Substance Registry System: METHYL 3-HYDROXYTETRADECANOATE(55682-83-2)

Safety Data

• Hazardous Substances Data: 55682-83-2(Hazardous Substances Data)

Usage

Description

METHYL 3-HYDROXYTETRADECANOATE, also known as 3-hydroxy Myristic acid methyl ester, is a hydroxylated fatty acid methyl ester that has been found in E. camaldulensis and E. torelliana extracts. It is a volatile compound that contributes to the aroma of red wild strawberries (F. pentaphylla) but is not present in cultivated strawberries (Fragaria x ananassa). It is active against M. tuberculosis (MIC = 49.5 μg/ml) and is non-cytotoxic to Vero cells (IC50 = >100 μM).

Uses

Used in Pharmaceutical Industry:
METHYL 3-HYDROXYTETRADECANOATE is used as an active compound for its antimicrobial properties, specifically against M. tuberculosis.
Used in Flavor and Fragrance Industry:
METHYL 3-HYDROXYTETRADECANOATE is used as a volatile compound for its contribution to the aroma of red wild strawberries.
Used in Chemical Synthesis:
METHYL 3-HYDROXYTETRADECANOATE is used as a starting material in the preparation of (S)-3-hydroxytetradecanoic acid and synthesis of unnatural analogs of lipid A containing the (S)-acid.

InChI:InChI=1/C15H30O3/c1-3-4-5-6-7-8-9-10-11-12-14(16)13-15(17)18-2/h14,16H,3-13H2,1-2H3

Synthetic route

methyl 3-oxotetradecanoate (22348-97-6) → (+/-)-3-hydroxytetradecanoic acid methyl ester (55682-83-2)

Conditions	Yield
With sodium tetrahydroborate In methanol at 0℃;	86%
With sodium tetrahydroborate In methanol at 5 - 10℃; for 2h;
With sodium tetrahydroborate In tetrahydrofuran; methanol

Dodecanal (112-54-9) + bromoacetic acid methyl ester (96-32-2) → (+/-)-3-hydroxytetradecanoic acid methyl ester (55682-83-2)

Conditions	Yield
With zinc In benzene for 2h; Heating;	82%

lauric acid (143-07-7) + monomethoxy poly(ethylene glycol) → (+/-)-3-hydroxytetradecanoic acid methyl ester (55682-83-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: tetrahydrofuran / 0 - 20 °C 2: 14.72 g / 72 h / 20 °C 3: 86 percent / sodium borohydride / methanol / 0 °C View Scheme

N-laurylimidazole (3867-67-2) → (+/-)-3-hydroxytetradecanoic acid methyl ester (55682-83-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: 14.72 g / 72 h / 20 °C 2: 86 percent / sodium borohydride / methanol / 0 °C View Scheme

n-dodecanoyl chloride (112-16-3) + glycerol-1-caprinate-3-stearate → (+/-)-3-hydroxytetradecanoic acid methyl ester (55682-83-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: pyridine / CH2Cl2 / 0 deg C, 1 h then r.t., 4 h 2: 3 h / Heating 3: NaBH4 / methanol / 2 h / 5 - 10 °C View Scheme

3-oxomyristic acid (88222-72-4) → (+/-)-3-hydroxytetradecanoic acid methyl ester (55682-83-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: 3 h / Heating 2: NaBH4 / methanol / 2 h / 5 - 10 °C View Scheme

polyhydroxyalkanoate → C14H20O4 + 3-hydroxybutyric acid methyl ester (1487-49-6) + 3-hydroxyoctanoic acid methyl ester (7367-87-5) + methyl 3-hydroxydecanoate (62675-82-5) + β-hydroxydodecanoic acid methyl ester (72864-23-4) + (+/-)-3-hydroxytetradecanoic acid methyl ester (55682-83-2) + 3-hydroxy-5-phenyl-pentanoic acid methyl ester (129880-16-6)

Conditions	Yield
Product distribution / selectivity;

polyhydroxyalkanoate → C13H15FO4 + 3-hydroxybutyric acid methyl ester (1487-49-6) + 3-hydroxyoctanoic acid methyl ester (7367-87-5) + methyl 3-hydroxyhexanoate (21188-58-9) + methyl 3-hydroxydecanoate (62675-82-5) + 3-hydroxy valeric acid methyl ester (56009-31-5) + methyl 3-hydroxyheptanoate (15889-95-9) + methyl 3-hydroxy-nonanoate (83968-06-3) + β-hydroxydodecanoic acid methyl ester (72864-23-4) + (+/-)-3-hydroxytetradecanoic acid methyl ester (55682-83-2)

Conditions	Yield
Product distribution / selectivity;

...Expand

polyhydroxyalkanoate → C13H15FO4 + 3-hydroxybutyric acid methyl ester (1487-49-6) + 3-hydroxyoctanoic acid methyl ester (7367-87-5) + methyl 3-hydroxyhexanoate (21188-58-9) + methyl 3-hydroxydecanoate (62675-82-5) + β-hydroxydodecanoic acid methyl ester (72864-23-4) + (+/-)-3-hydroxytetradecanoic acid methyl ester (55682-83-2)

Conditions	Yield
Product distribution / selectivity;

polyhydroxyalkanoate → C13H15FO4 + 3-hydroxybutyric acid methyl ester (1487-49-6) + 3-hydroxyoctanoic acid methyl ester (7367-87-5) + methyl 3-hydroxyhexanoate (21188-58-9) + methyl 3-hydroxydecanoate (62675-82-5) + methyl 3-hydroxyheptanoate (15889-95-9) + methyl 3-hydroxy-nonanoate (83968-06-3) + β-hydroxydodecanoic acid methyl ester (72864-23-4) + (+/-)-3-hydroxytetradecanoic acid methyl ester (55682-83-2)

Conditions	Yield
Product distribution / selectivity;

...Expand

methyl 3-methoxytetradecanoate (62673-11-4) → (+/-)-3-hydroxytetradecanoic acid methyl ester (55682-83-2)

Conditions	Yield
With methanol; boron trifluoride at 80℃; for 0.0833333h;

methanol (67-56-1) + 3-hydroxytetradecanoic acid (1961-72-4) → (+/-)-3-hydroxytetradecanoic acid methyl ester (55682-83-2)

Conditions	Yield
With boron trifluoride at 105℃; for 0.75h;

methanol (67-56-1) + lipopolysaccharide from Sinorhizobium fredii HH103, rkpA → 27-hydroxy-octacosanoic acid methyl ester (775341-88-3) + 3-hydroxy-octadecanoic acid methyl ester (2420-36-2) + β-hydroxyhexadecanoic acid methyl ester (51883-36-4) + methyl 3-hydroxytridecanoate (150024-70-7) + Methyl-3-hydroxypentadecanoat (112538-88-2) + β-hydroxydodecanoic acid methyl ester (72864-23-4) + (+/-)-3-hydroxytetradecanoic acid methyl ester (55682-83-2) + Methyl 29-hydroxytriacontanoate + C18H36O3 + C20H40O3

Conditions	Yield
With hydrogenchloride In water at 80℃; for 16h;

...Expand

methanol (67-56-1) + lipopolysaccharide from Sinorhizobium fredii HH103, rkpM → 27-hydroxy-octacosanoic acid methyl ester (775341-88-3) + 3-hydroxy-octadecanoic acid methyl ester (2420-36-2) + β-hydroxyhexadecanoic acid methyl ester (51883-36-4) + methyl 3-hydroxytridecanoate (150024-70-7) + Methyl-3-hydroxypentadecanoat (112538-88-2) + β-hydroxydodecanoic acid methyl ester (72864-23-4) + (+/-)-3-hydroxytetradecanoic acid methyl ester (55682-83-2) + Methyl 29-hydroxytriacontanoate + C18H36O3 + C20H40O3

Conditions	Yield
With hydrogenchloride In water at 80℃; for 16h;

...Expand

(+/-)-3-hydroxytetradecanoic acid methyl ester (55682-83-2) + O-benzylhydoxylamine hydrochloride (2687-43-6) → 3-hydroxy-tetradecanoic acid benzyloxy-amide (444023-10-3)

Conditions	Yield
With trimethylaluminum In n-heptane; dichloromethane at 0 - 20℃;	85%

(+/-)-3-hydroxytetradecanoic acid methyl ester (55682-83-2) + allyl bromide (106-95-6) → (2RS,3SR)-2-allyl-3-hydroxytetradecanoic acid methyl ester

Conditions	Yield
Stage #1: (+/-)-3-hydroxytetradecanoic acid methyl ester With lithium diisopropyl amide In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: allyl bromide With N,N,N,N,N,N-hexamethylphosphoric triamide In tetrahydrofuran; hexane at -78℃; for 1h; Further stages.;	62%

(+/-)-3-hydroxytetradecanoic acid methyl ester (55682-83-2) → 3-hydroxytetradecanoic acid (1961-72-4)

Conditions	Yield
With sodium hydroxide In methanol Ambient temperature; Yield given;

Mosher's acid chloride (64312-89-6) + (+/-)-3-hydroxytetradecanoic acid methyl ester (55682-83-2) → 3-(3,3,3-Trifluoro-2-methoxy-2-phenyl-propionyloxy)-tetradecanoic acid methyl ester

Conditions	Yield
With pyridine

(+/-)-3-hydroxytetradecanoic acid methyl ester (55682-83-2) → (SR)-1-[(RS)-4-methylene-5-oxotetrahydrofuran-3-yl]dodecyl acetate

Conditions

Yield

Multi-step reaction with 7 steps 1.1: LDA / tetrahydrofuran; hexane / 1 h / -78 °C 1.2: 62 percent / hexamethylphosphoramide / tetrahydrofuran; hexane / 1 h / -78 °C 2.1: 68 percent / diisobutylaluminum hydride / CH2Cl2; hexane / 2 h / 0 - 20 °C 3.1: 76 percent / 4-(dimethylamino)pyridine; imidazole / CH2Cl2 / 3 h / 20 °C 4.1: 91 percent / 4-(dimethylamino)pyridine; triethylamine / CH2Cl2 / 2 h / 20 °C 5.1: ozone / CH2Cl2 / -78 °C 5.2: 78 percent / Et2NH / CH2Cl2 / 1.5 h / -78 - 20 °C 6.1: 72 percent / sodium chlorite; sodium dihydrogen phosphate dihydrate; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 2.5 h / 20 °C 7.1: 40 percent / trifluoroacetic acid / methanol / 0.5 h / 20 °C View Scheme

(+/-)-3-hydroxytetradecanoic acid methyl ester (55682-83-2) → [(2SR,3RS)-4-methylene-5-oxo-2-undecyltetrahydrofuran-3-yl]methyl acetate

Conditions

Yield

Multi-step reaction with 7 steps 1.1: LDA / tetrahydrofuran; hexane / 1 h / -78 °C 1.2: 62 percent / hexamethylphosphoramide / tetrahydrofuran; hexane / 1 h / -78 °C 2.1: 68 percent / diisobutylaluminum hydride / CH2Cl2; hexane / 2 h / 0 - 20 °C 3.1: 76 percent / 4-(dimethylamino)pyridine; imidazole / CH2Cl2 / 3 h / 20 °C 4.1: 91 percent / 4-(dimethylamino)pyridine; triethylamine / CH2Cl2 / 2 h / 20 °C 5.1: ozone / CH2Cl2 / -78 °C 5.2: 78 percent / Et2NH / CH2Cl2 / 1.5 h / -78 - 20 °C 6.1: 72 percent / sodium chlorite; sodium dihydrogen phosphate dihydrate; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 2.5 h / 20 °C 7.1: 40 percent / trifluoroacetic acid / methanol / 0.5 h / 20 °C View Scheme

(+/-)-3-hydroxytetradecanoic acid methyl ester (55682-83-2) → (SR)-4-[(RS)-1-hydroxydodecyl]-3-methylenedihydrofuran-2(3H)-one

Conditions	Yield
Multi-step reaction with 7 steps 1.1: LDA / tetrahydrofuran; hexane / 1 h / -78 °C 1.2: 62 percent / hexamethylphosphoramide / tetrahydrofuran; hexane / 1 h / -78 °C 2.1: 68 percent / diisobutylaluminum hydride / CH2Cl2; hexane / 2 h / 0 - 20 °C 3.1: 76 percent / 4-(dimethylamino)pyridine; imidazole / CH2Cl2 / 3 h / 20 °C 4.1: 91 percent / 4-(dimethylamino)pyridine; triethylamine / CH2Cl2 / 2 h / 20 °C 5.1: ozone / CH2Cl2 / -78 °C 5.2: 78 percent / Et2NH / CH2Cl2 / 1.5 h / -78 - 20 °C 6.1: 72 percent / sodium chlorite; sodium dihydrogen phosphate dihydrate; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 2.5 h / 20 °C 7.1: 42 percent / acetyl chloride / methanol / 0.5 h / 20 °C View Scheme
Multi-step reaction with 8 steps 1.1: LDA / tetrahydrofuran; hexane / 1 h / -78 °C 1.2: 62 percent / hexamethylphosphoramide / tetrahydrofuran; hexane / 1 h / -78 °C 2.1: 68 percent / diisobutylaluminum hydride / CH2Cl2; hexane / 2 h / 0 - 20 °C 3.1: 76 percent / 4-(dimethylamino)pyridine; imidazole / CH2Cl2 / 3 h / 20 °C 4.1: 91 percent / 4-(dimethylamino)pyridine; triethylamine / CH2Cl2 / 2 h / 20 °C 5.1: ozone / CH2Cl2 / -78 °C 5.2: 78 percent / Et2NH / CH2Cl2 / 1.5 h / -78 - 20 °C 6.1: 72 percent / sodium chlorite; sodium dihydrogen phosphate dihydrate; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 2.5 h / 20 °C 7.1: 94 percent / CH2Cl2; diethyl ether / 0.5 h / 20 °C 8.1: 52 percent / acetyl chloride / methanol / 0.5 h / 20 °C View Scheme

(+/-)-3-hydroxytetradecanoic acid methyl ester (55682-83-2) → (4RS,5SR)-4-hydroxymethyl-3-methylene-5-undecyldihydrofuran-2(3H)-one

Conditions	Yield
Multi-step reaction with 7 steps 1.1: LDA / tetrahydrofuran; hexane / 1 h / -78 °C 1.2: 62 percent / hexamethylphosphoramide / tetrahydrofuran; hexane / 1 h / -78 °C 2.1: 68 percent / diisobutylaluminum hydride / CH2Cl2; hexane / 2 h / 0 - 20 °C 3.1: 76 percent / 4-(dimethylamino)pyridine; imidazole / CH2Cl2 / 3 h / 20 °C 4.1: 91 percent / 4-(dimethylamino)pyridine; triethylamine / CH2Cl2 / 2 h / 20 °C 5.1: ozone / CH2Cl2 / -78 °C 5.2: 78 percent / Et2NH / CH2Cl2 / 1.5 h / -78 - 20 °C 6.1: 72 percent / sodium chlorite; sodium dihydrogen phosphate dihydrate; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 2.5 h / 20 °C 7.1: 42 percent / acetyl chloride / methanol / 0.5 h / 20 °C View Scheme
Multi-step reaction with 8 steps 1.1: LDA / tetrahydrofuran; hexane / 1 h / -78 °C 1.2: 62 percent / hexamethylphosphoramide / tetrahydrofuran; hexane / 1 h / -78 °C 2.1: 68 percent / diisobutylaluminum hydride / CH2Cl2; hexane / 2 h / 0 - 20 °C 3.1: 76 percent / 4-(dimethylamino)pyridine; imidazole / CH2Cl2 / 3 h / 20 °C 4.1: 91 percent / 4-(dimethylamino)pyridine; triethylamine / CH2Cl2 / 2 h / 20 °C 5.1: ozone / CH2Cl2 / -78 °C 5.2: 78 percent / Et2NH / CH2Cl2 / 1.5 h / -78 - 20 °C 6.1: 72 percent / sodium chlorite; sodium dihydrogen phosphate dihydrate; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 2.5 h / 20 °C 7.1: 94 percent / CH2Cl2; diethyl ether / 0.5 h / 20 °C 8.1: 36 percent / acetyl chloride / methanol / 0.5 h / 20 °C View Scheme

(+/-)-3-hydroxytetradecanoic acid methyl ester (55682-83-2) → (2RS,3SR)-2-allyltetradecane-1,3-diol

Conditions	Yield
Multi-step reaction with 2 steps 1.1: LDA / tetrahydrofuran; hexane / 1 h / -78 °C 1.2: 62 percent / hexamethylphosphoramide / tetrahydrofuran; hexane / 1 h / -78 °C 2.1: 68 percent / diisobutylaluminum hydride / CH2Cl2; hexane / 2 h / 0 - 20 °C View Scheme

(+/-)-3-hydroxytetradecanoic acid methyl ester (55682-83-2) → (4RS,5SR)-4-[(tert-butyldimethylsilyloxy)methyl]hexadec-1-en-5-ol

Conditions	Yield
Multi-step reaction with 3 steps 1.1: LDA / tetrahydrofuran; hexane / 1 h / -78 °C 1.2: 62 percent / hexamethylphosphoramide / tetrahydrofuran; hexane / 1 h / -78 °C 2.1: 68 percent / diisobutylaluminum hydride / CH2Cl2; hexane / 2 h / 0 - 20 °C 3.1: 76 percent / 4-(dimethylamino)pyridine; imidazole / CH2Cl2 / 3 h / 20 °C View Scheme

(+/-)-3-hydroxytetradecanoic acid methyl ester (55682-83-2) → (4RS,5SR)-4-[(tert-butyldimethylsilyloxy)methyl]hexadec-1-en-5-yl acetate

Conditions

Yield

Multi-step reaction with 4 steps 1.1: LDA / tetrahydrofuran; hexane / 1 h / -78 °C 1.2: 62 percent / hexamethylphosphoramide / tetrahydrofuran; hexane / 1 h / -78 °C 2.1: 68 percent / diisobutylaluminum hydride / CH2Cl2; hexane / 2 h / 0 - 20 °C 3.1: 76 percent / 4-(dimethylamino)pyridine; imidazole / CH2Cl2 / 3 h / 20 °C 4.1: 91 percent / 4-(dimethylamino)pyridine; triethylamine / CH2Cl2 / 2 h / 20 °C View Scheme

(+/-)-3-hydroxytetradecanoic acid methyl ester (55682-83-2) → (3RS,4SR)-3-[(tert-butyldimethylsilyloxy)methyl]-2-formylpentadec-1-en-4-yl acetate

Conditions

Yield

Multi-step reaction with 5 steps 1.1: LDA / tetrahydrofuran; hexane / 1 h / -78 °C 1.2: 62 percent / hexamethylphosphoramide / tetrahydrofuran; hexane / 1 h / -78 °C 2.1: 68 percent / diisobutylaluminum hydride / CH2Cl2; hexane / 2 h / 0 - 20 °C 3.1: 76 percent / 4-(dimethylamino)pyridine; imidazole / CH2Cl2 / 3 h / 20 °C 4.1: 91 percent / 4-(dimethylamino)pyridine; triethylamine / CH2Cl2 / 2 h / 20 °C 5.1: ozone / CH2Cl2 / -78 °C 5.2: 78 percent / Et2NH / CH2Cl2 / 1.5 h / -78 - 20 °C View Scheme

(+/-)-3-hydroxytetradecanoic acid methyl ester (55682-83-2) → (+/-)-trans-1-benzyl-3-(N-(1,1-dimethylethyl)amino)-4-undecyl-2-azetidinone

Conditions

Yield

Multi-step reaction with 6 steps 1: 85 percent / AlMe3 / CH2Cl2; heptane / 0 - 20 °C 2: 84 percent / triphenylphosphine; carbon tetrachloride; triethylamine / acetonitrile / 0 - 20 °C 3: H2 / Pd/C / methanol 4: 90 percent / diisopropylethylamine / acetonitrile / 0.5 h / 0 °C 5: 60 percent / DBU / acetonitrile / 47.5 h / 20 °C 6: 63 percent / NaH / dimethylformamide; various solvent(s) / 7 h / 0 - 20 °C View Scheme

(+/-)-3-hydroxytetradecanoic acid methyl ester (55682-83-2) → (+/-)-trans-1-(tert-butyldiphenylsilyl)-3-(N-(1,1-dimethylethyl)amino)-4-undecyl-2-azetidinone

Conditions

Yield

Multi-step reaction with 6 steps 1: 85 percent / AlMe3 / CH2Cl2; heptane / 0 - 20 °C 2: 84 percent / triphenylphosphine; carbon tetrachloride; triethylamine / acetonitrile / 0 - 20 °C 3: H2 / Pd/C / methanol 4: 90 percent / diisopropylethylamine / acetonitrile / 0.5 h / 0 °C 5: 60 percent / DBU / acetonitrile / 47.5 h / 20 °C 6: 32 percent / n-BuLi / tetrahydrofuran; hexane / 0.75 h / -78 °C View Scheme

(+/-)-3-hydroxytetradecanoic acid methyl ester (55682-83-2) → 1-hydroxy-4-undecyl-azetidin-2-one

Conditions	Yield
Multi-step reaction with 3 steps 1: 85 percent / AlMe3 / CH2Cl2; heptane / 0 - 20 °C 2: 84 percent / triphenylphosphine; carbon tetrachloride; triethylamine / acetonitrile / 0 - 20 °C 3: H2 / Pd/C / methanol View Scheme

(+/-)-3-hydroxytetradecanoic acid methyl ester (55682-83-2) → acetic acid 2-oxo-4-undecyl-azetidin-3-yl ester

Conditions	Yield
Multi-step reaction with 5 steps 1: 85 percent / AlMe3 / CH2Cl2; heptane / 0 - 20 °C 2: 84 percent / triphenylphosphine; carbon tetrachloride; triethylamine / acetonitrile / 0 - 20 °C 3: H2 / Pd/C / methanol 4: 90 percent / diisopropylethylamine / acetonitrile / 0.5 h / 0 °C 5: 28 percent / diisopropylethylamine / acetonitrile View Scheme

(+/-)-3-hydroxytetradecanoic acid methyl ester (55682-83-2) → (+/-)-trans-3-azido-4-undecyl-2-azetidinone

Conditions	Yield
Multi-step reaction with 5 steps 1: 85 percent / AlMe3 / CH2Cl2; heptane / 0 - 20 °C 2: 84 percent / triphenylphosphine; carbon tetrachloride; triethylamine / acetonitrile / 0 - 20 °C 3: H2 / Pd/C / methanol 4: 90 percent / diisopropylethylamine / acetonitrile / 0.5 h / 0 °C 5: 65 percent / trimethylsilyl azide; diisopropylethylamine / acetonitrile / 20 °C View Scheme

(+/-)-3-hydroxytetradecanoic acid methyl ester (55682-83-2) → (+/-)-trans-3-(N-(1,1-dimethylethyl)amino)-4-undecyl-2-azetidinone

Conditions	Yield
Multi-step reaction with 5 steps 1: 85 percent / AlMe3 / CH2Cl2; heptane / 0 - 20 °C 2: 84 percent / triphenylphosphine; carbon tetrachloride; triethylamine / acetonitrile / 0 - 20 °C 3: H2 / Pd/C / methanol 4: 90 percent / diisopropylethylamine / acetonitrile / 0.5 h / 0 °C 5: 60 percent / DBU / acetonitrile / 47.5 h / 20 °C View Scheme

Upstream product

• 143-07-7 lauric acid 
• 112-16-3 n-dodecanoyl chloride 
• 67-56-1 methanol 
• 1961-72-4 3-hydroxytetradecanoic acid 
• 62673-11-4 methyl 3-methoxytetradecanoate 
• 88222-72-4 3-oxomyristic acid 
• 3867-67-2 N-laurylimidazole 
• 112-54-9 Dodecanal 
• 96-32-2 bromoacetic acid methyl ester 
• 22348-97-6 methyl 3-oxotetradecanoate 

Downstream Products

• 1961-72-4 3-hydroxytetradecanoic acid 
• 76062-97-0 methyl (R)-3-hydroxytetradecanoate 
• 76835-67-1 (S)-methyl 3-hydroxymyristate 
• 131486-38-9 methyl (S)-3-acetoxytetradecanoate 
• 109357-47-3 C₂₂H₂₉F₅O₄ 
• 28715-21-1 (R)-3-hydroxytetradecanoic acid 
• 35683-15-9 (3S)-3-hydroxytetradecanoic acid 
• 444023-20-5 (+/-)-1-tosyloxy-4-undecyl-2-azetidinone 
• 444023-47-6 3-benzyl-4-undecyloxazolidine-2,5-dione 
• 444023-43-2 (+/-)-1-benzyl-3-oxo-4-undecyl-2-azetidinone 
• 444023-15-8 (+/-)-1-(O-benzyl)-4-undecyl-2-azetidinone 
• 444023-10-3 3-hydroxy-tetradecanoic acid benzyloxy-amide 

Relevant articles and documents

1-Acetyl-3-[(3R)-hydroxyfatty acyl]glycerols: Lipid Compounds from Euphrasia rostkoviana Hayne and E. tetraquetra (Bréb.) Arrond

Five homologous acetylated acylglycerols of 3-hydroxyfatty acids (chain lengths C(14) - C(18)), named euphrasianins A - E, were characterized for the first time in Euphrasia rostkoviana Hayne (Orobanchaceae) by gas chromatography/mass spectrometry (GC/MS) and high-performance liquid chromatography/atmospheric pressure chemical ionization-mass spectrometry (HPLC/APCI-MSn). In addition to mass spectrometric data, structures of euphrasianins were verified via a three-step total synthesis of one representative homologue (euphrasianin A). The structure of the latter was confirmed by 1D- and 2D-NMR experiments as well as high-resolution electrospray ionization-mass spectrometry (HR-ESI-MS). The absolute configuration of the 3-hydroxyfatty acid moiety at C(3) was found to be R in the natural euphrasianins, which was determined by alkaline hydrolysis and methylation of a purified fraction, followed by chiral GC analysis. Furthermore, in extracts of Euphrasia tetraquetra (Bréb.) Arrond. euphrasianins C and E were detected exclusively, indicating that this subclass of lipid constituents is possibly valuable for fingerprinting methods.

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The kinetic resolution of 3-hydroxy fatty acid esters C8:0 to C16:0 with Candida antarctica lipase B shows common plots of the enantiomeric excesses of the product and substrate, respectively, versus the conversion and an enantiomeric ratio E of 27 calculated from ee(p). Differences in E, either calculated from the products or the substrates, could be explained by competing oligomerization as a second substrate-consuming process. This reaction is slow compared to acylation, and the remaining enantiomer was oligomerized. Taylor & Francis Group, LLC.

Gas chromatography/electron-capture negative ion mass spectrometry for the quantitative determination of 2- and 3-hydroxy fatty acids in bovine milk fat

2- and 3-hydroxy fatty acids (2- and 3-OH-FAs) are bioactive substances reported in sphingolipids and bacteria. Little is known of their occurrence in food. For this reason, a method suitable for the determination of OH-FAs at trace levels in bovine milk fat was developed. OH-FAs (and conventional fatty acids in samples) were converted into methyl esters and the hydroxyl group was derivatized with pentafluorobenzoyl (PFBO) chloride to give PFBO-O-FA methyl esters. These derivatives with strong electron affinity were determined by gas chromatography interfaced to mass spectrometry using electron-capture negative ion in the selected ion monitoring mode (GC/ECNI-MS-SIM). This method proved to be highly sensitive and selective for PFBO-O-FA methyl esters. For the analysis of samples, two internal standards were used. For this purpose, 9,10-dideutero-2-OH-18:0 methyl ester (ISTD-1) from 2-OH-18:1(9c) methyl ester as well as the ethyl ester of 3-PFBO-O-12:0 (ISTD-2) was synthesized. ISTD-1 served as a recovery standard whereas ISTD-2 was used for GC/MS measurements. The whole-sample cleanup consisted of accelerated solvent extraction of dry bovine milk, addition of ISTD 1, saponification, conversion of fatty acids into methyl esters by use of boron trifluoride, separation of the methyl esters of OH-FAs from nonsubstituted FAs on activated silica, conversion of OH-FAs methyl esters into PFBO-O-FA methyl esters, addition of ISTD-2, and measurement by GC/ECNI-MS-SIM. By this method, ten OH-FAs were quantified in bovine milk fat with high precision in the range from 0.02 ± 0.00 to 4.49 ± 0.29 mg/100 g of milk fat.