9,10,16-Trihydroxy palmitic acid supplier

Name
ALEURITIC ACID
EINECS 232-692-7
CAS No. 533-87-9
Density 1.085 g/cm³
Solubility Soluble in water, alcohol, acetic acid and acetone.
Melting Point 100-101 °C(lit.)
Formula C16H32 O5
Boiling Point 516.7 °C at 760 mmHg
Molecular Weight 304.427
Flash Point 280.4 °C
Transport Information
Appearance white to beige crystalline powder
Safety Poison by intravenous route. When heated to decomposition it emits acrid smoke and irritating fumes.
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms Hexadecanoicacid, 9,10,16-trihydroxy-, (R*,S*)-(?à)- (8CI); (?à)-erythro-Aleuritic acid; DL-erythro-Aleuritic acid;NSC 7668; erythro-Aleuritic acid; a-Aleuritic acid
PSA 97.99000
LogP 2.46630

Synthetic route

: methyl aleuritate

: 533-87-9
erythro-9,10,16-trihydroxyhexadecanoic acid

Conditions

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

: 16-bromo-erythro-9.10-dihydroxy-palmitic acid

: 533-87-9
erythro-9,10,16-trihydroxyhexadecanoic acid

Conditions

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

: 16-acetoxy-9,10-dihydroxy-hexadecanoic acid ethyl ester

: 533-87-9
erythro-9,10,16-trihydroxyhexadecanoic acid

Conditions

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

: 1619-68-7, 17278-80-7, 18951-79-6
16-hydroxy-9-hexadecenoic acid

: 533-87-9
erythro-9,10,16-trihydroxyhexadecanoic acid

Conditions

Conditions	Yield
With formic acid; dihydrogen peroxide

: 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
threo-9,10,16-trihydroxyhexadecanoic acid

: 533-87-9
erythro-9,10,16-trihydroxyhexadecanoic acid

Conditions

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

: 79-21-0
peracetic acid

: 94676-70-7
16-acetoxy-hexadec-9-enoic acid ethyl ester

alcoholic NaOH: alcoholic NaOH

: 533-87-9
erythro-9,10,16-trihydroxyhexadecanoic acid

...Expand

: cis-16-iodo-hexadec-9-enoic acid ethyl ester

: 533-87-9
erythro-9,10,16-trihydroxyhexadecanoic acid

Conditions

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

: 533-87-9
erythro-9,10,16-trihydroxyhexadecanoic acid

Conditions

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

: 94676-70-7
16-acetoxy-hexadec-9-enoic acid ethyl ester

: 533-87-9
erythro-9,10,16-trihydroxyhexadecanoic acid

Conditions

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

: 99286-21-2
trans-16-bromo-9-hexadecenoic acid

: 533-87-9
erythro-9,10,16-trihydroxyhexadecanoic acid

Conditions

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

: 533-87-9
erythro-9,10,16-trihydroxyhexadecanoic acid

: 1619-68-7, 17278-80-7, 18951-79-6
16-hydroxy-9-hexadecenoic acid

Conditions

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

: 533-87-9
erythro-9,10,16-trihydroxyhexadecanoic acid

: 1619-68-7
16-Hydroxy-cis-hexadec-9-enoic acid

Conditions

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

: 64-17-5
ethanol

: 533-87-9
erythro-9,10,16-trihydroxyhexadecanoic acid

: DL-threo-9,10,16-trihydroxypalmitic acid ethyl ester

Conditions

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

: 533-87-9
erythro-9,10,16-trihydroxyhexadecanoic acid

: 101-70-2
bis(4-methoxyphenyl)amine

: (7S*,8R*)-15-(bis(4-methoxyphenyl)amino)pentadecane-1,7,8-triol

Conditions

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

: 186581-53-3, 908094-01-9
diazomethane

: 533-87-9
erythro-9,10,16-trihydroxyhexadecanoic acid

: methyl aleuritate

Conditions

Conditions	Yield
In methanol; diethyl ether

: 533-87-9
erythro-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
threo-9,10,16-trihydroxyhexadecanoic acid

Conditions

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

: 533-87-9
erythro-9,10,16-trihydroxyhexadecanoic acid

: 61668-05-1, 93416-17-2
(9R*,10S*)-9,10,16-triacetoxyhexadecanoic acid

Conditions

Conditions	Yield
acetylation;

: 533-87-9
erythro-9,10,16-trihydroxyhexadecanoic acid

: 108-24-7
acetic anhydride

: 61668-05-1, 93416-17-2
(9R*,10S*)-9,10,16-triacetoxyhexadecanoic acid

Conditions

Conditions	Yield
With pyridine for 8h; Heating;

: 533-87-9
erythro-9,10,16-trihydroxyhexadecanoic acid

: 10035-10-6, 12258-64-9
hydrogen bromide

: 64-19-7
acetic acid

β-9.10.16-tribromo-palmitic acid: β-9.10.16-tribromo-palmitic acid

...Expand

: 533-87-9
erythro-9,10,16-trihydroxyhexadecanoic acid

HBr: HBr

: 68373-00-2
9,10,16-tribromo-hexadecanoic acid

Conditions

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

: 533-87-9
erythro-9,10,16-trihydroxyhexadecanoic acid

: 1125-88-8
benzaldehyde dimethyl acetal

: 8-[(2S,4S,5R)-5-(6-Hydroxy-hexyl)-2-phenyl-[1,3]dioxolan-4-yl]-octanoic acid

Conditions

Conditions	Yield
With toluene-4-sulfonic acid

: 533-87-9
erythro-9,10,16-trihydroxyhexadecanoic acid

: 53837-83-5
Methyl-16-hydroxy-cis-9-hexadecenoat

Conditions

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

: 533-87-9
erythro-9,10,16-trihydroxyhexadecanoic acid

: 57491-60-8
methyl 16-acetoxy-hexadec-9(Z)-enoate

Conditions

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

: 533-87-9
erythro-9,10,16-trihydroxyhexadecanoic acid

: 16-Acetoxy-9,10-dibromo-hexadecanoic acid methyl ester

Conditions

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

: 533-87-9
erythro-9,10,16-trihydroxyhexadecanoic acid

: 57491-64-2
16-Iodo-(Z)-9-hexadecenoic acid

Conditions

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

: 533-87-9
erythro-9,10,16-trihydroxyhexadecanoic acid

: 373-49-9
cis-9-hexadecenoic acid

Conditions

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

: 533-87-9
erythro-9,10,16-trihydroxyhexadecanoic acid

: 1120-25-8
(Z)-9-hexadecenoic acid methyl ester

Conditions

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

: 533-87-9
erythro-9,10,16-trihydroxyhexadecanoic acid

: 34010-20-3
(Z)-hexadec-9-en-1-yl acetate

Conditions

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

: 533-87-9
erythro-9,10,16-trihydroxyhexadecanoic acid

: 57491-62-0
16-tosyloxy-(Z)-9-hexadecenoic acid

Conditions

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

: 533-87-9
erythro-9,10,16-trihydroxyhexadecanoic acid

: 10378-01-5
palmitoleyl alcohol

Conditions

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

: 533-87-9
erythro-9,10,16-trihydroxyhexadecanoic acid

: 40642-43-1
(Z)-tetradec-7-en-1-ol

Conditions

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

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

: 533-87-9
erythro-9,10,16-trihydroxyhexadecanoic acid

: 16974-10-0
1-acetoxy-(Z)-7-tetradecene

Conditions

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

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

: 533-87-9
erythro-9,10,16-trihydroxyhexadecanoic acid

: 49592-98-5
(Z)-methyl tetradec-7-enoate

Conditions

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

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

9,10,16-Trihydroxy palmitic acid Chemical Properties

Molecular Formula: C₁₆H₃₂O₅
Molar mass: 304.4223 g/mol
EINECS: 232-692-7
Density: 1.085 g/cm³
Flash Point: 280.4 °C
Index of Refraction: 1.498
Boiling Point: 516.7 °C at 760 mmHg
Vapour Pressure: 7.78E-13 mmHg at 25°C
Melting point: 100-101 °C(lit.)
Appearance: White to beige crystalline powder
Product categories: Fatty & Aliphatic Acids, Esters, Alcohols & Derivatives
Structure of 9,10,16-Trihydroxy palmitic acid (533-87-9):

XLogP3-AA: 2.5
H-Bond Donor: 4
H-Bond Acceptor: 5
Systematic Name: 9,10,16-Trihydroxyhexadecanoic acid
SMILES: O=C(O)CCCCCCCC(O)C(O)CCCCCCO
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)
InChIKey: MEHUJCGAYMDLEL-UHFFFAOYAO
Std. InChI: InChI=1S/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)
Std. InChIKey: MEHUJCGAYMDLEL-UHFFFAOYSA-N

9,10,16-Trihydroxy palmitic acid Toxicity Data With Reference

ivn-mus LD50:178 mg/kg

CSLNX* U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. (Aberdeen Proving Ground, MD 21010) NX#00691 .

Carcinogenicity of 9,10,16-Trihydroxy palmitic acid (533-87-9) hasn't been listed as a carcinogen by NTP, IARC,ACGIH, or CA Prop 65. And its toxicological properties have not been fully investigated.

9,10,16-Trihydroxy palmitic acid Consensus Reports

Reported in EPA TSCA Inventory.

9,10,16-Trihydroxy palmitic acid Safety Profile

Poison by intravenous route. When heated to decomposition it emits acrid smoke and irritating fumes.

Safety Statements:
22: Do not breathe dust
24: Avoid contact with skin
25: Avoid contact with eyes

9,10,16-Trihydroxy palmitic acid Specification

9,10,16-Trihydroxy palmitic acid (533-87-9) also can be called Aleuritolic acid ; Aleuritic acid ; erythro-Aleuritic acid ; beta-Aleuritic acid and DL-erythro-Aleuritic acid .It is hazardous,so the first aid measures and others should be known.Such as: When on the skin: first,should flush skin with plenty of water immediatelyfor at least 15 minutes while removing contaminated clothing. Secondly,Get shoesmedical aid . Or in the eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids.Then get medical aid soon.While ,it's Inhaled: Remove from exposure and move to fresh air immediately.Give artificial respiration while not breathing. When breathing is difficult, give oxygen. And as soon as to get medical aid. Then you have the ingesting of the product : If victim is conscious and alert, give 2-4 cupfuls of milk or water, and get medical aid immediately.
In addition, 9,10,16-Trihydroxy palmitic acid (533-87-9) can be stable under normal temperature and pressure conditions.It is not compatible with strong oxidizing agents, and you must not take it with incompatible materials.And also prevent it to broken down into hazardous decomposition products: irritating and toxic fumes and gases.Also known its polymerization is hazardous.

Product Name

ALEURITIC ACID

Synthetic route

9,10,16-Trihydroxy palmitic acid Chemical Properties

9,10,16-Trihydroxy palmitic acid Toxicity Data With Reference

9,10,16-Trihydroxy palmitic acid Consensus Reports

9,10,16-Trihydroxy palmitic acid Safety Profile

9,10,16-Trihydroxy palmitic acid Specification

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