506-46-7

Basic information

• Product Name: HEXACOSANOIC ACID
• Synonyms: Ceratinic acid;Ceratinicacid;Ceric acid;N-HEXACOSANOIC ACID;HEXACOSANOIC ACID APPROX. 95%;Ceroticacid=Cerotinoicacid;Cerotic acid, Cerotinic acid;Hexacosanoic acid,98%
• CAS NO: 506-46-7
• Molecular Formula: C₂₆H₅₂O₂
• Molecular Weight: 396.69
• EINECS: 208-040-2
• Product Categories: Alkylcarboxylic Acids;Biochemistry;Higher Fatty Acids & Higher Alcohols;Monofunctional & alpha,omega-Bifunctional Alkanes;Monofunctional Alkanes;Saturated Higher Fatty Acids;Aliphatics
• Mol File: 506-46-7.mol
• Article Data: 7

Chemical Properties

• Melting Point: 86-87 °C
• Boiling Point: 250 °C
• Flash Point: >110℃
• Appearance: White/Shiny Fluffy or Crystalline Powder
• Density: 0.81
• Vapor Pressure: 9.26E-08mmHg at 25°C
• Refractive Index: 1.4301
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly, Heated), Hexanes (Slightly, Heated)
• PKA: 4.78±0.10(Predicted)
• BRN: 1799681
• CAS DataBase Reference: HEXACOSANOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: HEXACOSANOIC ACID(506-46-7)
• EPA Substance Registry System: HEXACOSANOIC ACID(506-46-7)

Safety Data

• Safety Statements: 22-24/25
• Hazardous Substances Data: 506-46-7(Hazardous Substances Data)

Usage

Chemical Properties

white shiny fluffy or crystalline powder

Uses

Hexacosanoic acid may be used as a reference standard for the determination of hexacosanoic acid in human serum and plasma samples for the screening of peroxisomal disorders by gas chromatography-mass spectrometry (GC-MS) operating under selected-ion monitoring (SIM) modein biological samples by GC-MSin microalgal lipids by solid-phase extraction (SPE) followed by GC-MS analysisas a naphthoxyethyl derivative by high performance liquid chromatography (HPLC) coupled with fluorometric detection

Definition

ChEBI: A 26-carbon, straight-chain, saturated fatty acid.

General Description

Hexacosanoic acid is classified under the very long chain fatty acids (VLCFAs) group of biologically important compounds.

Purification Methods

Crystallise the acid from EtOH, aqueous EtOH and pet ether/Me2CO. [Beilstein 2 IV 1310.]

InChI:InChI=1/C26H52O2/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/h2-25H2,1H3,(H,27,28)

Synthetic route

hexacos-17c-enoic acid (66274-43-9) → 1-hexacosanoic acid (506-46-7)

Conditions	Yield
With platinum(IV) oxide; ethanol Hydrogenation;

hexacosyl alcohol (506-52-5) → 1-hexacosanoic acid (506-46-7)

Conditions	Yield
With chromium; acetic acid; benzene

E-hexacos-9-enoic acid (59708-77-9, 86901-41-9) → 1-hexacosanoic acid (506-46-7)

Conditions	Yield
Hydrogenation;

10-oxo-hexacosanoic acid (115385-33-6) → 1-hexacosanoic acid (506-46-7)

Conditions	Yield
With sodium hydroxide; hydrazine hydrate; ethylene glycol at 220℃;

13-oxo-hexacosanoic acid (115386-09-9) → 1-hexacosanoic acid (506-46-7)

Conditions	Yield
With potassium hydroxide; hydrazine hydrate; 2,2'-[1,2-ethanediylbis(oxy)]bisethanol at 200℃;
With sodium hydroxide; hydrazine hydrate In ethylene glycol

5-oxo-hexacosanoic acid methylamide (103099-72-5) → 1-hexacosanoic acid (506-46-7)

Conditions	Yield
With sodium; hydrazine hydrate; ethylene glycol at 200℃;

sebacic acid mono methyl ester (818-88-2) + stearic acid (57-11-4) → 1-hexacosanoic acid (506-46-7)

Conditions	Yield
With methanol; sodium Electrolysis.Behandlung des Reaktionsprodukts mit methanol.Natronlauge;

methyl hexacosanoate (5802-82-4) → 1-hexacosanoic acid (506-46-7)

Conditions	Yield
With sodium hydroxide In 1,4-dioxane; methanol

longamide → 1-hexacosanoic acid (506-46-7)

Conditions	Yield
saponification;

6-methyldotriacontane → 1-hexacosanoic acid (506-46-7) + n-heptacosanoic acid (7138-40-1)

Conditions	Yield
With chromium(VI) oxide In acetic acid at 80 - 90℃; for 4h;

nonacosanyl hexacosanoate → 1-hexacosanoic acid (506-46-7) + nonyl alcohol (143-08-8)

Conditions	Yield
With potassium hydroxide In ethanol for 4h; Hydrolysis; Heating;

1-hydroxy-pentacosane-carboxylic acid-(1) → 1-hexacosanoic acid (506-46-7)

Conditions	Yield
With phosphorus; hydrogen iodide; acetic acid at 125 - 130℃;

7-oxo-pentacosane-carboxylic acid-(1) → 1-hexacosanoic acid (506-46-7)

Conditions	Yield
With sodium hydroxide; hydrazine hydrate; 2,2'-[1,2-ethanediylbis(oxy)]bisethanol
With sodium hydroxide; hydrazine hydrate; diethylene glycol

tetrachloromethane (56-23-5) + 8-oxo-hexacosanoic acid (97075-39-3) + hydrazine hydrate (7803-57-8) + diethylene glycol (111-46-6) → 1-hexacosanoic acid (506-46-7)

tetrachloromethane (56-23-5) + 10-oxo-hexacosanoic acid (115385-33-6) + hydrazine hydrate (7803-57-8) + diethylene glycol (111-46-6) → 1-hexacosanoic acid (506-46-7)

9-oxo-pentacosane-carboxylic acid-(1) → 1-hexacosanoic acid (506-46-7)

Conditions	Yield
With sodium hydroxide; hydrazine hydrate; 2,2'-[1,2-ethanediylbis(oxy)]bisethanol
With sodium hydroxide; hydrazine hydrate; diethylene glycol

ethanol (64-17-5) + n-pentacosyl cyanide → 1-hexacosanoic acid (506-46-7)

Conditions	Yield
With sodium hydroxide

pentacosane-dicarboxylic acid-(1.1) → 1-hexacosanoic acid (506-46-7)

Conditions	Yield
at 140 - 150℃; im Hochvakuum;

ethanol (64-17-5) + hexacos-17c-enoic acid (66274-43-9) + PtO2 → 1-hexacosanoic acid (506-46-7)

Conditions	Yield
Hydrogenation;

N-methyladipinimide (25077-25-2) → 1-hexacosanoic acid (506-46-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: diethyl ether 2: hydrazine hydrate; ethylene glycol; sodium / 200 °C View Scheme

methyl 11-iodoundecanoate (929-33-9) → 1-hexacosanoic acid (506-46-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: pentan-2-one; potassium carbonate / Behandeln des Reaktionsprodukts in Benzol mit wss.-methanol. Kalilauge 2: hydrazine hydrate; potassium hydroxide; triethylene glycol / 200 °C View Scheme
Multi-step reaction with 2 steps 1: (i) Mg, (ii) MeI, CuI, (iii) /BRN= 1771478/ 2: aq. NaOH / methanol; dioxane View Scheme

methyl 3-oxohexadecanoate (14427-53-3) → 1-hexacosanoic acid (506-46-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: pentan-2-one; potassium carbonate / Behandeln des Reaktionsprodukts in Benzol mit wss.-methanol. Kalilauge 2: hydrazine hydrate; potassium hydroxide; triethylene glycol / 200 °C View Scheme

pentadecyl bromide (629-72-1) → 1-hexacosanoic acid (506-46-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: (i) Mg, (ii) MeI, CuI, (iii) /BRN= 1771478/ 2: aq. NaOH / methanol; dioxane View Scheme

2-Phenethyloxycarbonyl-tridecanedioic acid diphenethyl ester → 1-hexacosanoic acid (506-46-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: (i) NaOEt, benzene, (ii) /BRN= 636924/, (iii) H2, Pd-C, EtOAc, EtOH, Pd-SrCO3 2: N2H4*H2O, NaOH / ethane-1,2-diol View Scheme

tetradecanoyl chloride (112-64-1) → 1-hexacosanoic acid (506-46-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: (i) NaOEt, benzene, (ii) /BRN= 636924/, (iii) H2, Pd-C, EtOAc, EtOH, Pd-SrCO3 2: N2H4*H2O, NaOH / ethane-1,2-diol View Scheme

hexacosanenitrile (257298-80-9) → 1-hexacosanoic acid (506-46-7)

Conditions	Yield
Stage #1: hexacosanenitrile With sodium hydroxide; water In ethanol at 70℃; for 144h; Stage #2: With hydrogenchloride In ethanol; water pH=3; solid phase reaction;

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + 1-hexacosanoic acid (506-46-7) → hexacosanoic acid 2,5-dioxo-pyrrolidin-1-yl ester (22102-68-7)

Conditions	Yield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 40℃; for 5h;	100%
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 40℃; for 3h;	95%
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 40℃; for 3h; Inert atmosphere;	57%

1-hexacosanoic acid (506-46-7) → hexacosanoyl chloride (145411-41-2)

Conditions	Yield
With oxalyl dichloride In benzene at 60℃; for 1h;	100%
With oxalyl dichloride at 70℃; for 2h;
With oxalyl dichloride at 70℃; for 2h; Inert atmosphere;

D-ribo-phytosphingosine (554-62-1) + 1-hexacosanoic acid (506-46-7) → hexacosanoic acid (2,3-dihydroxy-1-hydroxymethyl-heptadecyl) amide (182362-51-2)

Conditions	Yield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 168h;	100%

2-amino-1-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-3,4-O-isopropylidene-D-ribo-1,3,4-tricosanetriol (918867-02-4) + 1-hexacosanoic acid (506-46-7) → 2-hexacosanoylamino-1-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-3,4-O-isopropylidene-D-ribo-1,3,4-tricosanetriol (918867-03-5)

Conditions	Yield
With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃; for 120h;	96%

1-hexacosanoic acid (506-46-7) + (2S,3S,4R)-[(R)-3,4-benzylidenedioxy]-2-hydroxyoctadecyl 2,3-di-O-(4-methoxybenzyl)-4,6-O-(di-tert-butylsilylene)-α-D-galactopyranoside → (2S,3R,4R)-[(R)-3,4-benzylidenedioxy]-2-(hexacosanoyloxy)octadecyl 2,3-di-O-(4-methoxybenzyl)-4,6-O-(di-tert-butylsilylene)-α-D-galactopyranoside

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran; dichloromethane at 20℃; for 96h;	95%

1-hexacosanoic acid (506-46-7) + (2R)-(-)-2-phenyl-2-(piperidin-1-yl)ethanol (154472-05-6) → (S)-1-phenyl-2-(piperidin-1-yl)ethyl hexacosanoate

Conditions	Yield
Stage #1: (2R)-(-)-2-phenyl-2-(piperidin-1-yl)ethanol With methanesulfonyl chloride; triethylamine In chloroform at 0 - 5℃; for 0.5h; Stage #2: 1-hexacosanoic acid With triethylamine In chloroform at 5 - 20℃; for 16h; enantiospecific reaction;	95%

1-hexacosanoic acid (506-46-7) + (2S,3S,4R)-(+)-2-amino-3,4-O-isopropylidenyloctadecane-1,3,4-triol (111466-50-3) → Hexacosanoic acid [(S)-1-((4S,5R)-2,2-dimethyl-5-tetradecyl-[1,3]dioxolan-4-yl)-2-hydroxy-ethyl]-amide (164070-38-6)

Conditions	Yield
With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline In ethanol at 50℃; for 12h;	94%
With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline	86%

1-hexacosanoic acid (506-46-7) + 1-((2'S,3'S,4'R)-2'-amino-1',3',4'-octadecanyl)-α-D-mannopyranoside-2,2,2-trifluoroacetate → N-[(1S,2S,3R)-2,3-dihydroxy-1-[(α-D-mannopyranosyloxy)methyl]heptadecyl]hexacosanamide

Conditions	Yield
Stage #1: 1-hexacosanoic acid With isopropyl chloroformate; triethylamine In dichloromethane at 20℃; Inert atmosphere; Stage #2: 1-((2'S,3'S,4'R)-2'-amino-1',3',4'-octadecanyl)-α-D-mannopyranoside-2,2,2-trifluoroacetate In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃; Inert atmosphere;	94%

1-hexacosanoic acid (506-46-7) + (2S,3S,4R)-2-hydroxy-3,4-O-isopropylideneoctadecyl-2,3-di-O-benzyl-4,6-O-benzylidene-α-D-galactopyranoside (1215176-85-4) → (2S,3R,4R)-2-hexacosanoyloxy-3,4-O-isopropylideneoctadecyl-2,3-di-O-benzyl-4,6-O-benzylidene-α-D-galactopyranoside (1215176-87-6)

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran; dichloromethane at 20℃; for 108h;	93%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran; dichloromethane at 20℃; for 120h;	93%

1-hexacosanoic acid (506-46-7) + (2S,3S,4R)-2-hydroxy-3,4-O-isopropylideneoctadecyl 2,3-di-O-benzyl-4,6-O-benzylidene-α-D-galactopyranoside → (2S,3R,4R)-2-hexacosanoyloxy-3,4-O-isopropylideneoctadecyl 2,3-di-O-benzyl-4,6-O-benzylidene-α-D-galactopyranoside

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran; dichloromethane at 20 - 30℃; for 120h;	93%

D-ribo-phytosphingosine (554-62-1) + 1-hexacosanoic acid (506-46-7) → C48H97NO4 (871541-12-7)

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 100℃; for 6h;	92%

1-hexacosanoic acid (506-46-7) + 3,4 di-O-benzylphytosphingosine (202812-11-1) → (2S,3S,4R)-2-hexacosylamino-3,4-di-O-benzyl-1,3,4-octadecanetriol (160280-70-6)

Conditions	Yield
With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In tetrahydrofuran	91%
With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline In ethanol at 50℃; for 12h;	86%
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; Inert atmosphere;	470 mg

1-hexacosanoic acid (506-46-7) + (2S,3S,4R)-3-benzyloxy-2-hydroxy-4-methoxyoctadecyl 2,3-di-O-benzyl-4,6-O-benzylidene-α-D-galactopyranoside (1242144-41-7) → (2S,3R,4R)-3-benzyloxy-2-hexacosanoyloxy-4-methoxyoctadecyl 2,3-di-O-benzyl-4,6-O-benzylidene-α-D-galactopyranoside (1242144-42-8)

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran; dichloromethane at 20℃; for 108h;	90%

1-hexacosanoic acid (506-46-7) + (1S,2S,3R)-2,3-Bis-benzyloxy-1-trityloxymethyl-heptadecylamine (160280-68-2) → (2S,3S,4R)-3,4-di-O-benzyl-N-hexacosanoyl-1-O-trityl-2-amino-3,4-octadecanetriol (160280-69-3)

Conditions	Yield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 2h; Heating;	88%
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 2h; Heating / reflux;	88%

(2S,3R,4S)-3-(tert-butyldimethylsilyloxy)-2-[(tert-butyldimethylsilyloxy)methyl]-4-tetradecylazetidine (908848-05-5) + 1-hexacosanoic acid (506-46-7) → (2S,3R,4S)-3-(tert-butyldimethylsilyloxy)-2-[(tert-butyldimethylsilyloxy)methyl]-4-tetradecyl-1-hexacosanoylazetidine (908848-06-6)

Conditions	Yield
With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 48h;	88%
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; dmap In dichloromethane at 20℃; for 62h;	72%
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; dmap In dichloromethane at 20℃; for 62h;	72%

1-hexacosanoic acid (506-46-7) + (2S,3S,4S,5R,6S)-2-amino-5,6-bis(tert-butyldimethylsilyloxy)-3,4-O-isopropylidene-3,4-dihydroxyoctadecyl 2,3-bis-O-(4-methoxybenzyl)-4,6-O-(di-tert-butyl)silylene-α-D-galactopyranoside (1428421-84-4) → (2S,3S,4S,5R,6S)-5,6-bis(tert-butyldimethylsilyloxy)-2-hexacosanoylamino-3,4-O-isopropylidene-3,4-dihydroxyoctadecyl 2,3-bis-O-(4-methoxybenzyl)-4,6-O-(di-tert-butyl)silylene-α-D-galactopyranoside (1428421-85-5)

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran; dichloromethane at 20℃; for 3h;	86%

1-hexacosanoic acid (506-46-7) + C66H79N5O8 (1354327-82-4) → C92H131N3O9 (1354327-83-5)

Conditions	Yield
Stage #1: C66H79N5O8 With triphenylphosphine In water; benzene at 60℃; Stage #2: 1-hexacosanoic acid With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran at 25℃; for 24h;	85%

(2S,3R,5S)-3-{(tert-butyldimethylsilyl)oxy}-2-[{(tert-butyldimethylsilyl)oxy}methyl]-5-tridecylpyrrolidine + 1-hexacosanoic acid (506-46-7) → (2S,3R,5S)-3-(tert-butyldimethylsilyloxy)-2-[(tert-butyldimethylsilyloxy)methyl]-5-tridecyl-1-hexacosanoylpyrrolidine

Conditions	Yield
With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 48h;	84%
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; dmap In dichloromethane at 20℃; for 42h;	77%

4-nitro-phenol (100-02-7) + 1-hexacosanoic acid (506-46-7) → cerotic acid para-nitrophenyl ester (205371-71-7)

Conditions	Yield
With dicyclohexyl-carbodiimide; dmap In dichloromethane at 20℃; for 16h; In the dark;	83%

1-hexacosanoic acid (506-46-7) + C68H77N3O8 → C94H127N3O9 (1354328-15-6)

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran at 20℃; for 24h; Inert atmosphere;	83%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran at 20℃; for 24h; Inert atmosphere;	31 mg

1-hexacosanoic acid (506-46-7) + [(E)-(S)-1-((4S,5R)-2,2-Dimethyl-5-tetradecyl-[1,3]dioxolan-4-yl)-3-((2R,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-allyl]-carbamic acid tert-butyl ester (799268-03-4) → C79H123NO8 (865880-62-2)

Conditions

Yield

Stage #1: [(E)-(S)-1-((4S,5R)-2,2-Dimethyl-5-tetradecyl-[1,3]dioxolan-4-yl)-3-((2R,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-allyl]-carbamic acid tert-butyl ester With triethylsilane; trifluoroacetic acid In dichloromethane at 0℃; for 2h; Stage #2: 1-hexacosanoic acid With dmap; benzotriazol-1-ol; diisopropyl-carbodiimide In N,N-dimethyl-formamide at 20℃; for 6h; Stage #3: With triethylamine In N,N-dimethyl-formamide at 20℃; Product distribution / selectivity;

80%

1-hexacosanoic acid (506-46-7) + (1R,2S,3S,4S,5S,6S)-2-((S)-2-amino-2-((4S,5R)-2,2-dimethyl-5-tetradecyl-1,3-dioxolan-4-yl)ethylamino)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)cyclohexanol (1319731-16-2) → N-((S)-1-((4S,5R)-2,2-dimethyl-5-tetradecyl-1,3-dioxolan-4-yl)-2-((1S,2S,3S,4S,5S,6R)-2,3,4-tris(benzyloxy)-5-(benzyloxymethyl)-6-hydroxycyclohexylamino)ethyl)cerotamide (1319731-41-3)

Conditions	Yield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran at 20℃; Reflux; Inert atmosphere;	79%

(2S,3S,4R)-1-O-(2,3-di-O-benzyl-4,6-O-benzylidene-α-D-galactopyranosyl)-2-azido-3,4-di-O-benzyl-octadecantriol + 1-hexacosanoic acid (506-46-7) → (2S,3S,4R)-1-O-(2,3-di-O-benzyl-4,6-O-benzylidene-α-D-galactopyranosyl)-2-hexacosanoyl-3,4-di-O-benzyl-octadecantriol

Conditions

Yield

Stage #1: (2S,3S,4R)-1-O-(2,3-di-O-benzyl-4,6-O-benzylidene-α-D-galactopyranosyl)-2-azido-3,4-di-O-benzyl-octadecantriol With triphenylphosphine In pyridine; water at 50℃; for 5h; Staudinger reaction; Stage #2: 1-hexacosanoic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In pyridine; dichloromethane; water at 20℃; for 22h; Further stages.;

78.1%

(2S,3R,5R)-3-(tert-butyldimethylsilyloxy)-2-[(tert-butyldimethylsilyloxy)methyl]-5-tridecylpyrrolidine (1017937-47-1) + 1-hexacosanoic acid (506-46-7) → (2S,3R,5R)-3-(tert-butyldimethylsilyloxy)-2-[(tert-butyldimethylsilyloxy)methyl]-5-tridecyl-1-hexacosanoylpyrrolidine (1017937-56-2)

Conditions	Yield
With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 48h;	78%

1-hexacosanoic acid (506-46-7) + (2R,4R)-2-amino-4-(benzyloxy)octadecan-1-ol (1309668-39-0) → N-((2R,4R)-4-(benzyloxy)-1-hydroxyoctadecan-2-yl)hexacosanamide (1309668-40-3)

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 6h; Inert atmosphere;	78%

C29H63NO2Si2 + 1-hexacosanoic acid (506-46-7) → (2S,3R,5S)-3-(tert-butyldimethylsilyloxy)-2-[(tert-butyldimethylsilyloxy)methyl]-5-tridecyl-1-hexacosanoylpyrrolidine

Conditions	Yield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; dmap In dichloromethane at 20℃; for 42h;	77%

1-hexacosanoic acid (506-46-7) + (2S,3S,4R)-2-hydroxy-3,4-O-isopropylideneoctadecyl 2,3,4-tri-O-benzyl-6-O-methyl-α-D-galactopyranoside (1242144-21-3) → (2S,3R,4R)-2-hexacosanoyloxy-3,4-O-isopropylideneoctadecyl 2,3,4-tri-O-benzyl-6-O-methyl-α-D-galactopyranoside (1242144-25-7)

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran; dichloromethane at 20℃; for 108h;	77%

(2S,3R,4E)-2-amino-3-O-para-methoxybenzyl-1-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-4-octadecene (853055-35-3) + 1-hexacosanoic acid (506-46-7) → C86H129NO9

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 3h;	77%

1-hexacosanoic acid (506-46-7) + 1,2-O-isopropylidene-D-glycerol (14347-78-5) → 1,2-O-isopropylidene-1-O-(hexacosanoyl)-sn-glycerol

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In toluene at 70℃;	73%

1-hexacosanoic acid (506-46-7) + (2S,3S,4R)-2-azido-3,4-O-isopropylidene-1-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-octadec-5-en-1,3,4-triol (1423041-19-3) → (2S,3S,4R)-2-hexacosanoylamino-3,4-O-isopropylidene-1-O-(2,3,4,6-tetra-O-benzyl-α-d-galactopyranosyl)-octadec-5-en-1,3,4-triol

Conditions	Yield
Stage #1: (2S,3S,4R)-2-azido-3,4-O-isopropylidene-1-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-octadec-5-en-1,3,4-triol With pyridine; triphenylphosphine In tetrahydrofuran at 20 - 60℃; for 12h; Stage #2: 1-hexacosanoic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine for 12h;	72%

Upstream product

• 66274-43-9 hexacos-17c-enoic acid 
• 506-52-5 hexacosyl alcohol 
• 59708-77-9 E-hexacos-9-enoic acid 
• 115385-33-6 10-oxo-hexacosanoic acid 
• 115386-09-9 13-oxo-hexacosanoic acid 
• 103099-72-5 5-oxo-hexacosanoic acid methylamide 
• 818-88-2 sebacic acid mono methyl ester 
• 57-11-4 stearic acid 
• 5802-82-4 methyl hexacosanoate 
• 56-23-5 tetrachloromethane 
• 97075-39-3 8-oxo-hexacosanoic acid 
• 7803-57-8 hydrazine hydrate 
• 111-46-6 diethylene glycol 
• 64-17-5 ethanol 

Downstream Products

• 5802-82-4 methyl hexacosanoate 
• 1054644-79-9 Hexacosanoic acid ((1S,2S,3R)-2,3-bis-benzyloxy-1-benzyloxymethyl-heptadecyl)-amide 
• 160280-69-3 (2S,3S,4R)-3,4-di-O-benzyl-N-hexacosanoyl-1-O-trityl-2-amino-3,4-octadecanetriol 
• 160280-70-6 (2S,3S,4R)-2-hexacosylamino-3,4-di-O-benzyl-1,3,4-octadecanetriol 
• 158021-47-7 KRN₇₀₀₀ 
• 22102-68-7 hexacosanoic acid 2,5-dioxo-pyrrolidin-1-yl ester 
• 176020-22-7 (2S,3S,4R)-3,4-di-O-benzyl-N-hexacosanoyl-1-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-2-amino-1,3,4-octadecanetriol 
• 930283-75-3 3,4-di-O-benzyl-2-hexacosylamino-1-O-triisopropylsilyl-octadec-6-ene 
• 930283-70-8 3,4-di-O-benzyl-1-O-(2-O-benzyl-4,6-O-benzylidene-α-D-galactopyranosyl)-2-hexacosylamino-D-ribo-octadec-6-en-1-ol 
• 886034-83-9 2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl-(1->3)-2,4,6-tri-O-pivaloyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-pivaloyl-β-D-glucopyranosyl-(1->1)-(2S,3R,4E)-2-hexacosanoylamino-3-O-(4-methoxybenzyl)-4-octadecen-1,3-diol 
• 956102-18-4 C₇₂H₁₀₉NO₉ 

Relevant articles and documents

MINOR AMIDES OF PIPER SPECIES

Three new pyrrolidides, brachyamide A, brachyamide B and brachystine, have been isolated from Piper brachystachyum.The known amides, pipercide, retrofractamide A, and guineensine, the lignans pluviatilol, methyl pluviatilol (fargesin), sesamine, asarinine and the aromatic hydrocarbon pipataline, substituted cinnamic acids, methyl ester and sitosterol were also isolated and identified.Piper longum furnished a new long chain isobutyl amide, longamide, besides guineensine and the same lignans as isolated from P. brachystachyum.All the new piperamides were characterized by spectral studies and chemical degradation.Key Word Index-Piper Brachystachyum, P. longum; Piperaceae; pyrrolidides; brachyamide A; brachyamide B; brachystine, longamide; retrofractamide A; isobutyl amides; lignans; cinnamic acid derivatives; sitosterol.

Morpholinones as light stabilizers

The invention relates to new compounds containing 1-8 active groups of the type 3,3,6,6-polysubstituted 2-morpholinone and having the formula F(A'-Z)m-X(F),wherein m is a number from 1 to 8; X is an organic anchor group of valency m and in case that m is not 1, X may also be a direct bond, SO2, P or PO; A' is a monovalent group of the formula E containing one linking group; Z is a direct bond, -O-, -S-, -SO-, -SO2- or -NR'14-; provided that Z is -O-, -S-, -SO-, -SO2- or -NR'14- if m is 1 and the linking group in formula E is G3 or G5; G1 is hydrogen; C1-C18alkyl; C2-C18alkyl substituted by OH and/or phenyl; oxyl; OH; C2-C12cyanoalkyl; C2-C12cyanoalkoxy; C1-C18alkoxy; C5-C12cycloalkoxy; C3-C8alkenyl; C3-C8alkynyl; C3-C8alkenyloxy; C7-C12phenylalkyl; C7-C12phenylalkyl substituted by hydroxy, C1-C4alkyl and/or C1-C4alkoxy; C7-C15phenylalkoxy; C7-C15phenylalkoxy, which is substituted by C1-C4alkyl and/or C1-C4alkoxy; or G1 is C1-C8alkanoyl; C3-C5alkenoyl; C1-C18alkanoyloxy; C3-C8epoxyalkyl; or G1 is the linking group -R10-; G2 and G4 are, independently of one another, C1-C18alkyl, C5-C12cycloalkenyl, C5-C12cycloalkyl, or an oligocyclic hydrocarbon residue of 6-12 carbon atoms; G3 is as defined for G2 or is C1-C8hydroxyalkyl; or G2 and G3 together are (CH2)e, where e is a number from 4 to 11; or G5 is the linking group -R5-; G5 is as defined for G4 or is C1-C8hydroxyalkyl; or G4 and G5 together are (CH2)e, where e is number from 4 to 11; or G5 is the linking group -R5-; G6 is as defined for G4 or is hydrogen; or G6 is the linking group, which is a direct bond or -R5-; and other residues are as defined in claim 1. The new compounds are effective as stabilizers for organic material, especially coatings, against harmful effects of light, oxygen and/or heat.

ALIPHATIC CONSTITUENTS FROM DUBOISIA MYOPOROIDES

Four new compounds, isolated from the leaves and stem of Duboisia myoproides have been characterized as 6-methyldotriacontane, hentriacontanyl tetratriacontanoate, 3-hydroxydotriacontan-28-one and 4-pentatriacontanone, respectively, by spectral data and chemical studies.Key Word Index - Duboisia myoporoides; Solanaceae; leaves and stems; 6-methyldotriacontane; hentriacontanyl tetratriacontanoate; 3-hydroxydotriacontan-28-one; 4-pentatriacontanone.