533-87-9

Basic information

• Product Name: ALEURITIC ACID
• Synonyms: 8,9,15-trihydroxypentadecane-1-carboxylicacid;9,10,16-trihydroxy-,(r*,s*)-(+-)-hexadecanoicaci;9,10,16-trihydroxy-,(R*,S*)-(±)-Hexadecanoicacid;9,10,16-trihydroxy-,(theta,s)-(+/-)-hexadecanoicaci;aleuriticacid,tech.;alpha-aleuriticacid;DL-erythro-9,10,16-Trihydroxyhexadecanoic acid;dl-erythro-9,10,16-trihydroxyhexadecanoicacid
• CAS NO: 533-87-9
• Molecular Formula: C₁₆H₃₂O₅
• Molecular Weight: 304.42
• EINECS: 232-692-7
• Product Categories: Fatty & Aliphatic Acids, Esters, Alcohols & Derivatives;Building Blocks;C13 to C42+;Carbonyl Compounds;Carboxylic Acids;Chemical Synthesis;Organic Building Blocks;Inhibitors
• Mol File: 533-87-9.mol
• Article Data: 5

Chemical Properties

• Melting Point: 100-101 °C(lit.)
• Boiling Point: 365.24°C (rough estimate)
• Flash Point: 280.4 °C
• Appearance: White to beige/Crystalline Powder
• Density: 1.085
• Vapor Pressure: 7.78E-13mmHg at 25°C
• Refractive Index: 1.6200 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly, Heated), DMSO (Slightly), Ethyl Acetate (Slightly, Heated,
• PKA: 4.78±0.10(Predicted)
• Water Solubility: Soluble in water, alcohol, acetic acid and acetone.
• Stability: Hygroscopic
• Merck: 14,231
• BRN: 1727724
• CAS DataBase Reference: ALEURITIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: ALEURITIC ACID(533-87-9)
• EPA Substance Registry System: ALEURITIC ACID(533-87-9)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• RTECS: ML9850000
• TSCA: Yes
• Hazardous Substances Data: 533-87-9(Hazardous Substances Data)

Usage

Chemical Properties

white to beige crystalline powder

Uses

α-Aleuritic acid is a major ingredient of shellac and is also a starting reagent in the manufacture of perfumes.

Purification Methods

Crystallise the acid from aqueous EtOH. The hydrazide crystallises from EtOH and has m 139-140o. [Beilstein 3 III 901.]

InChI:InChI=1/C16H32O5/c17-13-9-5-4-7-11-15(19)14(18)10-6-2-1-3-8-12-16(20)21/h14-15,17-19H,1-13H2,(H,20,21)/t14-,15-/m0/s1

Synthetic route

methyl aleuritate → erythro-9,10,16-trihydroxyhexadecanoic acid (533-87-9)

Conditions	Yield
With sodium hydroxide In N,N-dimethyl-formamide for 1h; Ambient temperature;	94%

16-bromo-erythro-9.10-dihydroxy-palmitic acid → erythro-9,10,16-trihydroxyhexadecanoic acid (533-87-9)

Conditions	Yield
With silver(I) acetate; acetic acid Erwaermen des Reaktionsprodukts mit 25prozentiger Kalilauge;

16-acetoxy-9,10-dihydroxy-hexadecanoic acid ethyl ester → erythro-9,10,16-trihydroxyhexadecanoic acid (533-87-9)

Conditions	Yield
With potassium hydroxide Hydrolysis;
With sodium hydroxide Hydrolysis;

16-hydroxy-9-hexadecenoic acid (1619-68-7, 17278-80-7, 18951-79-6) → erythro-9,10,16-trihydroxyhexadecanoic acid (533-87-9)

Conditions	Yield
With formic acid; dihydrogen peroxide

threo-9,10,16-trihydroxyhexadecanoic acid (533-87-9, 6949-98-0, 17941-34-3, 18299-27-9, 18951-77-4, 33098-98-5, 33098-99-6, 37179-76-3, 37179-77-4) → erythro-9,10,16-trihydroxyhexadecanoic acid (533-87-9)

Conditions	Yield
(i) aq. HCl, (ii) aq. NaOH; Multistep reaction;
With potassium hydroxide; hydrogen bromide; acetic acid Yield given. Multistep reaction;
Multi-step reaction with 2 steps 1: PhCO2H, HC(OEt)3 / (heating) 2: aq. H2O2, HCO2H View Scheme

peracetic acid (79-21-0) + 16-acetoxy-hexadec-9-enoic acid ethyl ester (94676-70-7) + alcoholic NaOH → erythro-9,10,16-trihydroxyhexadecanoic acid (533-87-9)

cis-16-iodo-hexadec-9-enoic acid ethyl ester → erythro-9,10,16-trihydroxyhexadecanoic acid (533-87-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: glacial acetic acid 2: H2O2; glacial acetic acid / 80 °C 3: alcoholic NaOH / Hydrolysis View Scheme

16-chloro-hexadec-9-enoic acid ethyl ester → erythro-9,10,16-trihydroxyhexadecanoic acid (533-87-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: glacial acetic acid 2: H2O2; glacial acetic acid / 80 °C 3: alcoholic NaOH / Hydrolysis View Scheme

16-acetoxy-hexadec-9-enoic acid ethyl ester (94676-70-7) → erythro-9,10,16-trihydroxyhexadecanoic acid (533-87-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: H2O2; glacial acetic acid / 80 °C 2: alcoholic NaOH / Hydrolysis View Scheme

trans-16-bromo-9-hexadecenoic acid (99286-21-2) → erythro-9,10,16-trihydroxyhexadecanoic acid (533-87-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: H2O2; glacial acetic acid / 70 - 80 °C 2: silver acetate; glacial acetic acid / Erwaermen des Reaktionsprodukts mit 25prozentiger Kalilauge View Scheme

erythro-9,10,16-trihydroxyhexadecanoic acid (533-87-9) → 16-hydroxy-9-hexadecenoic acid (1619-68-7, 17278-80-7, 18951-79-6)

Conditions	Yield
With 1H-imidazole; iodine; chloro-diphenylphosphine In 1,4-dioxane; toluene for 4h;	92%

erythro-9,10,16-trihydroxyhexadecanoic acid (533-87-9) → 16-Hydroxy-cis-hexadec-9-enoic acid (1619-68-7)

Conditions	Yield
With orthoformic acid triethyl ester; benzoic acid for 5h; Heating;	90%
With orthoformic acid triethyl ester; benzoic acid Heating;	88%
With orthoformic acid triethyl ester; benzoic acid (heating);
With phosphonium iodide; acetic acid	0.56 g

ethanol (64-17-5) + erythro-9,10,16-trihydroxyhexadecanoic acid (533-87-9) → DL-threo-9,10,16-trihydroxypalmitic acid ethyl ester

Conditions	Yield
With sulfuric acid for 2h; Reflux;	71%

erythro-9,10,16-trihydroxyhexadecanoic acid (533-87-9) + bis(4-methoxyphenyl)amine (101-70-2) → (7S*,8R*)-15-(bis(4-methoxyphenyl)amino)pentadecane-1,7,8-triol

Conditions	Yield
With di-tert-butyl peroxide; copper(II) hexafluoroacetylacetonate; 9-mesitylacridine In ethyl acetate at 35℃; for 36h; Inert atmosphere; Irradiation;	54%

diazomethane (186581-53-3, 908094-01-9) + erythro-9,10,16-trihydroxyhexadecanoic acid (533-87-9) → methyl aleuritate

Conditions	Yield
In methanol; diethyl ether

erythro-9,10,16-trihydroxyhexadecanoic acid (533-87-9) → threo-9,10,16-trihydroxyhexadecanoic acid (533-87-9, 6949-98-0, 17941-34-3, 18299-27-9, 18951-77-4, 33098-98-5, 33098-99-6, 37179-76-3, 37179-77-4)

Conditions	Yield
(i) aq. HCl, (ii) aq. NaOH; Multistep reaction;

erythro-9,10,16-trihydroxyhexadecanoic acid (533-87-9) → (9R*,10S*)-9,10,16-triacetoxyhexadecanoic acid (61668-05-1, 93416-17-2)

Conditions	Yield
acetylation;

erythro-9,10,16-trihydroxyhexadecanoic acid (533-87-9) + acetic anhydride (108-24-7) → (9R*,10S*)-9,10,16-triacetoxyhexadecanoic acid (61668-05-1, 93416-17-2)

Conditions	Yield
With pyridine for 8h; Heating;

erythro-9,10,16-trihydroxyhexadecanoic acid (533-87-9) + hydrogen bromide (10035-10-6, 12258-64-9) + acetic acid (64-19-7) → β-9.10.16-tribromo-palmitic acid

erythro-9,10,16-trihydroxyhexadecanoic acid (533-87-9) + HBr → 9,10,16-tribromo-hexadecanoic acid (68373-00-2)

Conditions	Yield
With acetic acid at 80 - 100℃; β-form;

erythro-9,10,16-trihydroxyhexadecanoic acid (533-87-9) + benzaldehyde dimethyl acetal (1125-88-8) → 8-[(2S,4S,5R)-5-(6-Hydroxy-hexyl)-2-phenyl-[1,3]dioxolan-4-yl]-octanoic acid

Conditions	Yield
With toluene-4-sulfonic acid

erythro-9,10,16-trihydroxyhexadecanoic acid (533-87-9) → Methyl-16-hydroxy-cis-9-hexadecenoat (53837-83-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 88 percent / triethyl orthoformate, benzoic acid / Heating 2: 80 percent / BF3*Et2O / 0.25 h / Heating View Scheme

erythro-9,10,16-trihydroxyhexadecanoic acid (533-87-9) → methyl 16-acetoxy-hexadec-9(Z)-enoate (57491-60-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: 88 percent / triethyl orthoformate, benzoic acid / Heating 2: 80 percent / BF3*Et2O / 0.25 h / Heating 3: 91 percent / pyridine / 0.75 h / Heating View Scheme

erythro-9,10,16-trihydroxyhexadecanoic acid (533-87-9) → 16-Acetoxy-9,10-dibromo-hexadecanoic acid methyl ester

Conditions	Yield
Multi-step reaction with 4 steps 1: 88 percent / triethyl orthoformate, benzoic acid / Heating 2: 80 percent / BF3*Et2O / 0.25 h / Heating 3: 91 percent / pyridine / 0.75 h / Heating 4: AlCl3, Br2, NaN3, CH3CN / 6 h / Ambient temperature View Scheme

erythro-9,10,16-trihydroxyhexadecanoic acid (533-87-9) → 16-Iodo-(Z)-9-hexadecenoic acid (57491-64-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: 0.56 g / phosphonium iodide, AcOH 2: 0.51 g / pyridine / 15 h / -5 °C 3: 0.30 g / NaI / acetone / 16 h / Heating View Scheme

erythro-9,10,16-trihydroxyhexadecanoic acid (533-87-9) → cis-9-hexadecenoic acid (373-49-9)

Conditions	Yield
Multi-step reaction with 4 steps 1: 0.56 g / phosphonium iodide, AcOH 2: 0.51 g / pyridine / 15 h / -5 °C 3: 0.30 g / NaI / acetone / 16 h / Heating 4: 0.26 g / NaBH4 / dimethylformamide / 1 h / 80 °C View Scheme

erythro-9,10,16-trihydroxyhexadecanoic acid (533-87-9) → (Z)-9-hexadecenoic acid methyl ester (1120-25-8)

Conditions	Yield
Multi-step reaction with 5 steps 1: 0.56 g / phosphonium iodide, AcOH 2: 0.51 g / pyridine / 15 h / -5 °C 3: 0.30 g / NaI / acetone / 16 h / Heating 4: 0.26 g / NaBH4 / dimethylformamide / 1 h / 80 °C 5: 0.19 g / conc. H2SO4 / 6 h / Heating View Scheme

erythro-9,10,16-trihydroxyhexadecanoic acid (533-87-9) → (Z)-hexadec-9-en-1-yl acetate (34010-20-3)

Conditions	Yield
Multi-step reaction with 7 steps 1: 0.56 g / phosphonium iodide, AcOH 2: 0.51 g / pyridine / 15 h / -5 °C 3: 0.30 g / NaI / acetone / 16 h / Heating 4: 0.26 g / NaBH4 / dimethylformamide / 1 h / 80 °C 5: 0.19 g / conc. H2SO4 / 6 h / Heating 6: 0.14 g / LiAlH4 / tetrahydrofuran / 24 h / Ambient temperature 7: 0.1 g / pyridine / 25 h / Ambient temperature View Scheme

erythro-9,10,16-trihydroxyhexadecanoic acid (533-87-9) → 16-tosyloxy-(Z)-9-hexadecenoic acid (57491-62-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 0.56 g / phosphonium iodide, AcOH 2: 0.51 g / pyridine / 15 h / -5 °C View Scheme

erythro-9,10,16-trihydroxyhexadecanoic acid (533-87-9) → palmitoleyl alcohol (10378-01-5)

Conditions	Yield
Multi-step reaction with 6 steps 1: 0.56 g / phosphonium iodide, AcOH 2: 0.51 g / pyridine / 15 h / -5 °C 3: 0.30 g / NaI / acetone / 16 h / Heating 4: 0.26 g / NaBH4 / dimethylformamide / 1 h / 80 °C 5: 0.19 g / conc. H2SO4 / 6 h / Heating 6: 0.14 g / LiAlH4 / tetrahydrofuran / 24 h / Ambient temperature View Scheme

erythro-9,10,16-trihydroxyhexadecanoic acid (533-87-9) → (Z)-tetradec-7-en-1-ol (40642-43-1)

Conditions

Yield

Multi-step reaction with 8 steps 1: pyridine / 8 h / Heating 2: 69 percent / cupric acetate, lead tetraacetate / pyridine / 4 h / Heating 3: 1.) KMnO4, adogen 464, 2.) aq. NaOH / 1) water, benzene, 12 h, room temperature; 2) reflux, 3 h 4: 92 percent / triethyl orthoformate, benzoic acid / Heating 5: conc. H2SO4 / Heating 6: 92 percent / pyridine / 20 h / -5 °C 7: 80 percent / zinc (dust), NaI / 2.5 h / Heating 8: 85 percent / LAH / tetrahydrofuran / 4 h / Heating View Scheme

erythro-9,10,16-trihydroxyhexadecanoic acid (533-87-9) → 1-acetoxy-(Z)-7-tetradecene (16974-10-0)

Conditions

Yield

Multi-step reaction with 9 steps 1: pyridine / 8 h / Heating 2: 69 percent / cupric acetate, lead tetraacetate / pyridine / 4 h / Heating 3: 1.) KMnO4, adogen 464, 2.) aq. NaOH / 1) water, benzene, 12 h, room temperature; 2) reflux, 3 h 4: 92 percent / triethyl orthoformate, benzoic acid / Heating 5: conc. H2SO4 / Heating 6: 92 percent / pyridine / 20 h / -5 °C 7: 80 percent / zinc (dust), NaI / 2.5 h / Heating 8: 85 percent / LAH / tetrahydrofuran / 4 h / Heating 9: 90 percent / pyridine / 8 h / Ambient temperature View Scheme

erythro-9,10,16-trihydroxyhexadecanoic acid (533-87-9) → (Z)-methyl tetradec-7-enoate (49592-98-5)

Conditions

Yield

Multi-step reaction with 7 steps 1: pyridine / 8 h / Heating 2: 69 percent / cupric acetate, lead tetraacetate / pyridine / 4 h / Heating 3: 1.) KMnO4, adogen 464, 2.) aq. NaOH / 1) water, benzene, 12 h, room temperature; 2) reflux, 3 h 4: 92 percent / triethyl orthoformate, benzoic acid / Heating 5: conc. H2SO4 / Heating 6: 92 percent / pyridine / 20 h / -5 °C 7: 80 percent / zinc (dust), NaI / 2.5 h / Heating View Scheme

Upstream product

• 79-21-0 peracetic acid 
• 94676-70-7 16-acetoxy-hexadec-9-enoic acid ethyl ester 
• 533-87-9 DL-threo-9RS,10RS,16-trihydroxyhexadecanoic acid 
• 99286-21-2 trans-16-bromo-9-hexadecenoic acid 
• 533-87-9 threo-9,10,16-trihydroxyhexadecanoic acid 
• 1619-68-7 16-hydroxy-9-hexadecenoic acid 

Downstream Products

• 2027-46-5 threo-9.10-dihydroxy-palmitic acid 
• 1619-68-7 16-hydroxy-9-hexadecenoic acid 
• 533-87-9 threo-9,10,16-trihydroxyhexadecanoic acid 
• 533-87-9 DL-erythro-aleuritic acid 
• 54045-02-2 (3S,3aS,4S,7R,8S,8aS)-3-Formyl-4-((Z)-16-hydroxy-hexadec-9-enoyloxy)-8-hydroxymethyl-8-methyl-2,3,4,7,8,8a-hexahydro-1H-3a,7-methano-azulene-6-carboxylic acid 
• 1437766-19-2 C₂₅H₂₈N₆S₂ 
• 4944-60-9 1,9-nonanediol diacetate 
• 3937-56-2 1,9-Nonanediol 
• 53939-27-8 (Z)-9-tetradecenal 
• 35153-15-2 (Z)-9-tetradecen-1-ol 
• 16974-10-0 1-acetoxy-(Z)-7-tetradecene 
• 40642-43-1 (Z)-tetradec-7-en-1-ol 
• 20056-92-2 (Z)-7-dodecenol 
• 10378-01-5 palmitoleyl alcohol 

Relevant articles and documents

Preparation method of erythro-aleuritic acid

The invention provides a preparation method of erythro-aleuritic acid. The preparation method comprises the following steps: taking threo-aleuritic acid as a raw material, carrying out twice heating reflux and acid precipitation treatment to obtain erythro-aleuritic acid. Erythro-aleuritic acid is prepared through configuration conversion of threo-aleuritic acid, and a product is analyzed and confirmed by adopting characterization means such as FTIR, mass spectrum, nuclear magnetism, TG, DSC, XRD, chiral resolution, optical activity and the like. FTIR, mass spectrum, and nuclear magnetism showthat the structure of the product is consistent with that of threo-aleuritic acid; XRD, DSC and TG results show that the crystal form of threo-aleuritic acid is the same as that of the product, but the melting point of the product is higher, and the cell size is smaller; chiral resolution shows that the product is an optical isomer of aleuritic acid, that is, the product is determined to be erythro-aleuritic acid. The disclosed method can be used for effectively converting threo-aleuritic acid into erythro-aleuritic acid, and is high in conversion efficiency, high in yield of erythro-aleuritic acid and high in purity of erythro-aleuritic acid.

Reactions of olefinic ester derivatives of aleuritic acid: Part II-Synthesis of 5'-methyltetrazoles

Methyl 16-acetoxy-threo-9/10-bromo-10/9-(5'-methyl-1H-tetrazol-1-yl)hexadecanoate (6) and methyl 16-acetoxy-9/10-(5'-methyl-1H-tetrazol-1-yl)hexadec-9(E)-enoate (7) have been prepared from methyl 16-acetoxyhexadec-9(Z)-enoate, obtained from the naturally occurring threo-aleuritic acid.

Reactions of olefinic ester derivatives of aleuritic acid with iodonium nitrate

Methyl threo-16-acetoxy-9(10)-iodo-10(9)-nitratohexadecanoate (VII) and methyl threo-16-acetoxy-9(10)-iodo-10(9)-hydroxyhexadecanoate (VIII) have been prepared by reacting methyl 16-acetoxyhexadec-cis-9-enoate (VI) which in turn has been prepared from thr