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9,10,16-Trihydroxy palmitic acid

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Name

9,10,16-Trihydroxy palmitic acid

EINECS 232-692-7
CAS No. 533-87-9 Density 1.085 g/cm3
PSA 97.99000 LogP 2.46630
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 N/A Appearance white to beige crystalline powder
Safety Poison by intravenous route. When heated to decomposition it emits acrid smoke and irritating fumes. Risk Codes N/A
Molecular Structure Molecular Structure of 533-87-9 (ALEURITIC ACID) Hazard Symbols N/A
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

 

9,10,16-Trihydroxy palmitic acid Synthetic route

methyl aleuritate

533-87-9

erythro-9,10,16-trihydroxyhexadecanoic acid

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With formic acid; dihydrogen peroxide
533-87-9

erythro-9,10,16-trihydroxyhexadecanoic acid

Conditions
ConditionsYield
(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

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

533-87-9

erythro-9,10,16-trihydroxyhexadecanoic acid

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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

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

1.    

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.

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