506-13-8

Basic information

• Product Name: 16-HYDROXYHEXADECANOIC ACID
• Synonyms: Hexadecanoic acid, 16-hydroxy-;JUNIPERIC ACID;16-HYDROXYHEXADECANOIC ACID;16-HYDROXYPALMITIC ACID;16-hydroxy-hexadecanoicaci;16-Hydroxyhexadecanoic acid, 97+%;16-Hydroxyhexadecanoicacid,98%;16-Hydroxypalmitic acid, Juniperic acid
• CAS NO: 506-13-8
• Molecular Formula: C₁₆H₃₂O₃
• Molecular Weight: 272.42
• EINECS: 208-028-7
• Product Categories: omega-Functional Alkanols, Carboxylic Acids, Amines & Halides;omega-Hydroxycarboxylic Acids;Biochemicals and Reagents;Building Blocks;C13 to C42+;Carbonyl Compounds;Carboxylic Acids;Chemical Synthesis;Fatty Acids and conjugates;Fatty Acyls;Hydroxy Fatty Acids;Lipids;Organic Building Blocks
• Mol File: 506-13-8.mol
• Article Data: 18

Chemical Properties

• Melting Point: 94-98 °C(lit.)
• Boiling Point: 414.4 °C at 760 mmHg
• Flash Point: 218.6 °C
• Appearance: White/Crystalline Powder
• Density: 0.956g/cm³
• Vapor Pressure: 1.34E-08mmHg at 25°C
• Storage Temp.: 2-8°C
• PKA: 4.78±0.10(Predicted)
• BRN: 1783998
• CAS DataBase Reference: 16-HYDROXYHEXADECANOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 16-HYDROXYHEXADECANOIC ACID(506-13-8)
• EPA Substance Registry System: 16-HYDROXYHEXADECANOIC ACID(506-13-8)

Safety Data

• Statements: 36/37/38
• Safety Statements: 22-24/25
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 506-13-8(Hazardous Substances Data)

Usage

Description

16-hydroxy Hexadecanoic acid is a metabolite of the saturated fatty acid palmitic acid (16:0) that has been hydroxylated on its terminal (ω) carbon. It is produced by ω-hydroxylation of palmitic acid by cytochrome P450 in both plants and animals. In plants, it is commonly a component of cutin.

Chemical Properties

white crystalline powder

Uses

16-Hydroxyhexadecanoic acid was used in the synthesis of dihydroxypalmitic acids. It was also used to induce the expression of two GRP genes of Arabidopsis thaliana, AtGRP5 and AtGRP23.

Definition

ChEBI: A C16 omega-hydroxy fatty acid and key monomer of cutin in the plant cuticle.

InChI:InChI=1/C16H32O3/c17-15-13-11-9-7-5-3-1-2-4-6-8-10-12-14-16(18)19/h17H,1-15H2,(H,18,19)/p-1

Synthetic route

16-hydroxy-9-hexadecenoic acid (1619-68-7, 17278-80-7, 18951-79-6) → 16-hydroxyhexadecanoic acid (506-13-8)

Conditions	Yield
With hydrogen; palladium on activated charcoal	100%
With hydrogen; palladium on activated charcoal

16-Hydroxy-hexadeca-10,12-diynoic acid (91544-43-3) → 16-hydroxyhexadecanoic acid (506-13-8)

Conditions	Yield
With hydrogen; platinum(IV) oxide In methanol under 760 Torr; for 1h;	98%

15-hexadecanolide (109-29-5) → 16-hydroxyhexadecanoic acid (506-13-8)

Conditions	Yield
With water; tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide In toluene at 95℃; for 6h;	97%
With potassium hydroxide; polystyrene-CH2=O(CH2CH2O)6.4H copolymer In hexane at 70℃; for 5h;	96%
With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate In benzene at 70℃;	85%

iron(III)-acetylacetonate (14024-18-1) + 1-Hexadecanol (36653-82-4) → 4-hydroxy-5-methylpentan-2-one (56072-26-5) + hexadecyl acetate (629-70-9) + 16-hydroxyhexadecanoic acid (506-13-8) + iron(III) oxide

Conditions	Yield
at 80 - 300℃; under 760.051 Torr; for 2h; Green chemistry;	A n/a B n/a C n/a D 95%

16-Hydroxy-cis-hexadec-9-enoic acid (1619-68-7) → 16-hydroxyhexadecanoic acid (506-13-8)

Conditions	Yield
With hydrogen; palladium on activated charcoal In ethanol	80%

15-hexadecanolide (109-29-5) + (Z)-9-octadecen-1-amine (112-90-3) → 16-hydroxyhexadecanoic acid (506-13-8) + N-oleyl-16-hydroxyhexadecanoylamine (1220909-16-9)

Conditions	Yield
With lipase PS from Pseudomonas cepacia; water In Hexadecane at 60℃; for 24h; Miniemulsion system; Enzymatic reaction;	A 77% B 14%

Hexadecane (544-76-3) → 16-hydroxyhexadecanoic acid (506-13-8)

Conditions	Yield
(microbiological transformation);

adipic acid monomethyl ester (627-91-8) + 12-acetoxydodecanoic acid (100912-48-9) → 16-hydroxyhexadecanoic acid (506-13-8)

Conditions	Yield
(i) Na, MeOH, (electrolysis), (ii) KOH, EtOH; Multistep reaction;

azelaic acid monoethyl ester (1593-55-1) + 9-acetoxy nonanoic acid (30993-88-5) → 16-hydroxyhexadecanoic acid (506-13-8)

Conditions	Yield
(i) (electrochemical oxidation), aq. K2CO3, (ii) KOH, EtOH; Multistep reaction;

azelaic acid monoethyl ester (1593-55-1) + 9-Isovaleroyloxy-nonansaeure-(1) → 16-hydroxyhexadecanoic acid (506-13-8)

Conditions	Yield
(i) (electrochemical oxidation), aq. K2CO3, (ii) KOH, EtOH; Multistep reaction;

heptadec-16-enoic acid (65119-97-3) → 16-hydroxyhexadecanoic acid (506-13-8)

Conditions	Yield
(i) O3, (ii) NaBH4, KOH; Multistep reaction;

16-hydroxyhexadecanoic acid methyl ester (36575-67-4) → 16-hydroxyhexadecanoic acid (506-13-8)

Conditions	Yield
(saponification);

15-Carboxy-12-oxopentadecan-1-ol (3974-33-2) → 16-hydroxyhexadecanoic acid (506-13-8)

Conditions	Yield
With hydrogenchloride; mercury; zinc

16-Hydroxy-hexadecin-(12)-saeure (93158-27-1) → 16-hydroxyhexadecanoic acid (506-13-8)

Conditions	Yield
With hydrogen; palladium on activated charcoal In ethanol

16-Acetoxy-8-oxo-hexadecanoic acid methyl ester (112657-63-3) → 16-hydroxyhexadecanoic acid (506-13-8)

Conditions	Yield
With potassium hydroxide; hydrazine hydrate In diethylene glycol

16-Acetoxy-10-oxo-hexadecansaeure-(1)-methylester (112553-37-4) → 16-hydroxyhexadecanoic acid (506-13-8)

Conditions	Yield
With potassium hydroxide; hydrazine hydrate In diethylene glycol

16-Hydroxy-hexadecin-(9)-saeure (18941-99-6) → 16-hydroxyhexadecanoic acid (506-13-8)

Conditions	Yield
With hydrogen; platinum(IV) oxide In diethyl ether Yield given;

16-(Tetrahydro-pyran-2-yloxy)-hexadecanenitrile (103687-90-7) → 16-hydroxyhexadecanoic acid (506-13-8)

Conditions	Yield
With sodium hydroxide; toluene-4-sulfonic acid 1.) methanol; 2.) reflux; Yield given. Multistep reaction;

wax of thuja occidentalis → 12-hydroxydodecanoic acid (505-95-3) + 16-hydroxyhexadecanoic acid (506-13-8)

Conditions	Yield
durch Verseifen;

ω-oxy-Δξ-hexadecanoic acid → 16-hydroxyhexadecanoic acid (506-13-8)

Conditions	Yield
With acetic acid; platinum
With acetic acid; platinum

hexadecanediol-(1.16)-monoacetate → 16-hydroxyhexadecanoic acid (506-13-8)

Conditions	Yield
With chromic acid; acetic acid beim Verseifen der erhaltenen Acetyljuniperinsaeure;

16-hydroxy-hexadec-7-enoic acid (506-14-9) + acetic acid (64-19-7) + platinum → 16-hydroxyhexadecanoic acid (506-13-8)

Conditions	Yield
unter Druck.Hydrogenation;

wax of coniferin → 16-hydroxyhexadecanoic acid (506-13-8)

Conditions	Yield
durch Verseifen;

thapsic acid dimethyl ester → 16-hydroxyhexadecanoic acid (506-13-8) + hexadecanediol-(1.16)-monoacetate

Conditions	Yield
With ethanol; sodium

1,12-dibromododecane (3344-70-5) → 16-hydroxyhexadecanoic acid (506-13-8)

Conditions	Yield
Multi-step reaction with 4 steps 1: 1.) 1.6 M BuLi / 1.) THF, hexane, 10 deg C, HMPT, 1 h; 2.) THF, 20-25 deg C 2: 96 percent / hydrogen / PtO2 / ethyl acetate / 15 h 3: 89 percent / tributylamine / 24 h / Heating 4: 1.) TsOH; 2.) 10 N NaOH / 1.) methanol; 2.) reflux View Scheme

ω-bromo-1-[(tetrahydro-2H-pyran-2-yl)oxy]pentadecane (103687-89-4) → 16-hydroxyhexadecanoic acid (506-13-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 89 percent / tributylamine / 24 h / Heating 2: 1.) TsOH; 2.) 10 N NaOH / 1.) methanol; 2.) reflux View Scheme

2-(15-Bromo-pentadec-2-ynyloxy)-tetrahydro-pyran (103687-88-3) → 16-hydroxyhexadecanoic acid (506-13-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: 96 percent / hydrogen / PtO2 / ethyl acetate / 15 h 2: 89 percent / tributylamine / 24 h / Heating 3: 1.) TsOH; 2.) 10 N NaOH / 1.) methanol; 2.) reflux View Scheme

1 ,6-dibromohexane (629-03-8) + <4>pyridyl-methyl potassium → 16-hydroxyhexadecanoic acid (506-13-8)

Conditions	Yield
Multi-step reaction with 4 steps 1: NaOEt / ethanol; diethyl ether / 48 h / Ambient temperature 2: 48percent HBr / H2O / 4 h / 120 - 150 °C 3: 76 percent / LiNH2, Fe(NO3)3 / tetrahydrofuran; NH3 / 20 h 4: H2 / PtO2 / diethyl ether View Scheme

methanol (67-56-1) + 16-hydroxyhexadecanoic acid (506-13-8) → 16-hydroxyhexadecanoic acid methyl ester (36575-67-4)

Conditions	Yield
With acetyl chloride	100%
With toluene-4-sulfonic acid	100%
With toluene-4-sulfonic acid at 20℃; for 16h; Inert atmosphere;	100%

16-hydroxyhexadecanoic acid (506-13-8) + N,N'-bis(trimethylsilyl)urea (18297-63-7) → 16-Trimethylsilanyloxy-hexadecanoic acid

Conditions	Yield
tetrabutyl ammonium fluoride In dichloromethane at 0℃; for 1h;	100%

16-hydroxyhexadecanoic acid (506-13-8) + n-octanoic acid chloride (111-64-8) → 16-(octanoyloxy)hexadecanoic acid

Conditions	Yield
In chloroform for 4h; Reflux;	100%
In chloroform at 70℃; for 4h;	100%

16-hydroxyhexadecanoic acid (506-13-8) → 16-bromohexadecanoic acid (2536-35-8)

Conditions	Yield
With hydrogen bromide In acetic acid for 72h; Heating;	99%
With hydrogen bromide In acetic acid for 72h; Substitution; Heating;	99%
With sodium hydroxide; sulfuric acid; nitrogen; hydrogen bromide In acetic acid	88%

16-hydroxyhexadecanoic acid (506-13-8) → 16-iodohexadecanoic acid (2536-36-9)

Conditions	Yield
With chloro-trimethyl-silane; sodium iodide In acetonitrile	98%
With chloro-trimethyl-silane; sodium iodide In acetonitrile at 70℃; for 1.5h;	97%
With phosphorus; iodine

16-hydroxyhexadecanoic acid (506-13-8) + allyl bromide (106-95-6) → 16-hydroxyhexadecanoic acid allyl ester (275808-63-4)

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 23℃; for 48h; Addition;	98%

16-hydroxyhexadecanoic acid (506-13-8) → 15-hexadecanolide (109-29-5)

Conditions	Yield
With dmap; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In tetrahydrofuran; chloroform for 18h; Reflux; Inert atmosphere;	97%
With dmap; 4-(dimethylamino)pyridine hydrochloride; dicyclohexyl-carbodiimide In tetrahydrofuran; chloroform Heating;	96%
With dmap; polymer bound carbodiimide; 4-(dimethylamino)pyridine hydrochloride In tetrahydrofuran; chloroform Cyclization; lactonisation; Heating;	96%

16-hydroxyhexadecanoic acid (506-13-8) + 4,4'-dimethoxytrityl chloride (40615-36-9) → 16-O-(4,4'-dimethoxytrityl)hexadecanoic acid

Conditions	Yield
With pyridine; triethylamine at 20℃; for 3h; Inert atmosphere;	97%

diazomethane (186581-53-3, 908094-01-9) + 16-hydroxyhexadecanoic acid (506-13-8) → 16-hydroxyhexadecanoic acid methyl ester (36575-67-4)

Conditions	Yield
In methanol	95%
In diethyl ether at 0℃; for 2h;	95%
In dichloromethane

ethanol (64-17-5) + 16-hydroxyhexadecanoic acid (506-13-8) → ethyl 16-hydroxyhexadecanoate (85258-69-1)

Conditions	Yield
With acetyl chloride at 20℃; for 4h;	94%
With acetyl chloride Heating;

2,3,4,6-tetra-O-benzoyl-D-glucopyranosyl ortho-(hex-1-ynyl)benzoate (1221151-98-9) + 16-hydroxyhexadecanoic acid (506-13-8) → C50H58O12 (1221152-26-6)

Conditions	Yield
With 2,6-di-tert-butyl-pyridine; trifluoromethanesulfonyloxy(triphenylphosphine)gold(I) In dichloromethane at 20℃; Molecular sieve; Inert atmosphere; chemoselective reaction;	94%

16-hydroxyhexadecanoic acid (506-13-8) + acetyl chloride (75-36-5) → ethyl 16-hydroxyhexadecanoate (85258-69-1)

Conditions	Yield
In ethanol at 20℃; for 4h;	94%

16-hydroxyhexadecanoic acid (506-13-8) → 15-hexadecanolide (109-29-5) + 1,18-dioxo-17,34-dioxacyclotetratricontane (660-65-1)

Conditions	Yield
With p-nitrobenzoic anhydride; scandium tris(trifluoromethanesulfonate) In tetrahydrofuran; acetonitrile Heating; Yields of byproduct given;	A 92% B n/a
With dmap; iodine; di-2-thienyl carbonate In toluene; acetonitrile for 10h; Heating;	A 92% B n/a
With dmap; di-2-thienyl carbonate; hafnium(IV) trifluoromethanesulfonate In toluene; acetonitrile at 100℃; for 5h;	A 91% B n/a

16-hydroxyhexadecanoic acid (506-13-8) + glycerol (56-81-5) → 2,3-dihydroxypropyl 16-hydroxyhexadecanoate

Conditions	Yield
With mesoporous silica HMS2-SO3H at 110℃; for 15h; Product distribution; Further Variations:; Reagents; reaction times;	91%
With dmap; dicyclohexyl-carbodiimide In dichloromethane; N,N-dimethyl-formamide at 20℃; for 24h;

2,3,4-tri-O-acetyl-L-rhamnopyranosyl ortho-hexynylbenzoate (1230076-22-8) + 16-hydroxyhexadecanoic acid (506-13-8) → C28H48O10 (1221152-45-9)

Conditions	Yield
With trifluoromethanesulfonyloxy(triphenylphosphine)gold(I); boron trifluoride diethyl etherate; 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 20℃; Molecular sieve; Inert atmosphere; chemoselective reaction;	90%

16-hydroxyhexadecanoic acid (506-13-8) + ethanethiol (75-08-1) → 16-hydroxy-hexadecanethioic acid S-ethyl ester (66921-94-6)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 10h;	87%
With dmap; dicyclohexyl-carbodiimide

16-hydroxyhexadecanoic acid (506-13-8) + 1,1,1,3,3,3-hexamethyl-disilazane (999-97-3) → C22H48O3Si2 (93472-41-4)

Conditions	Yield
With pyridine; chloro-trimethyl-silane In dichloromethane at 60℃;	87%

16-hydroxyhexadecanoic acid (506-13-8) + benzoyl chloride (98-88-4) → 16-benzoyloxyhexadecanoic acid (173288-97-6)

Conditions	Yield
With triethylamine In dichloromethane for 0.5h; Ambient temperature;	87%

16-hydroxyhexadecanoic acid (506-13-8) → poly(16-hydroxyhexadecanoic acid), Mn: 38000, Mw/Mn: 2.6; Monomer(s): 16-hydroxyhexadecanoic acid

Conditions	Yield
With 4 A molecular sieve; immobilized lipase from Candida antarctica (CA; Novozym 435) In toluene at 70℃; under 140 - 150 Torr; for 6h; Enzymatic reaction;	85%

2,3,4,6-tetra-O-benzoyl-D-glucopyranosyl ortho-(hex-1-ynyl)benzoate (1221151-98-9) + 16-hydroxyhexadecanoic acid (506-13-8) → C50H58O12 (1221152-23-3)

Conditions	Yield
With trifluoromethanesulfonyloxy(triphenylphosphine)gold(I); boron trifluoride diethyl etherate; 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 20℃; Molecular sieve; Inert atmosphere; chemoselective reaction;	84%

16-hydroxyhexadecanoic acid (506-13-8) + N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) → 16-hydroxy-N-methoxy-N-methylhexadecanamide (288851-53-6)

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0 - 20℃; for 4h;	83%

16-hydroxyhexadecanoic acid (506-13-8) + cyanoacetic acid (372-09-8) → 16-(2-Cyano-acetoxy)-hexadecanoic acid

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 25℃; for 2h;	78%

16-hydroxyhexadecanoic acid (506-13-8) + L-homocysteine thiolactone hydrochloride (31828-68-9) → 16-hydroxy-hexadecanoyl-homocysteine thiolactone amide

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 72h; Molecular sieve;	78%

16-hydroxyhexadecanoic acid (506-13-8) + tert-butylchlorodiphenylsilane (58479-61-1) → 16-O-(tert-butyldiphenylsilyl)hexadecanoic acid

Conditions	Yield
With pyridine; 1H-imidazole; triethylamine In dichloromethane; N,N-dimethyl-formamide; toluene at 20℃; for 2h; Inert atmosphere;	78%

Upstream product

• 109-29-5 15-hexadecanolide 
• 544-76-3 Hexadecane 
• 627-91-8 adipic acid monomethyl ester 
• 100912-48-9 12-acetoxydodecanoic acid 
• 1593-55-1 azelaic acid monoethyl ester 
• 30993-88-5 9-acetoxy nonanoic acid 
• 65119-97-3 heptadec-16-enoic acid 
• 93158-27-1 16-Hydroxy-hexadecin-⁽¹²⁾-saeure 
• 112657-63-3 16-Acetoxy-8-oxo-hexadecanoic acid methyl ester 
• 112553-37-4 16-Acetoxy-10-oxo-hexadecansaeure-⁽¹⁾-methylester 
• 1619-68-7 16-hydroxy-9-hexadecenoic acid 
• 1619-68-7 16-Hydroxy-cis-hexadec-9-enoic acid 
• 3344-70-5 1,12-dibromododecane 
• 533-87-9 threo-9,10,16-trihydroxyhexadecanoic acid 

Downstream Products

• 3109-58-8 16-fluorohexadecanoic acid 
• 97462-92-5 16-p-toluenesulfonyloxyhexadecanoic acid 
• 92270-01-4 16-Hydroxy-hexadecanoic acid 4-nitro-phenyl ester 
• 328935-28-0 methyl 16-(4-vinylphenoxy)hexadecanoate 
• 328935-21-3 methyl 16-(4-vinylphenoxy)octadecanoate 
• 328935-25-7 methyl 16-(4-vinylphenoxy)docosanoate 
• 221623-65-0 16-Acetylsulfanyl-hexadecanoic acid (S)-1-benzyloxymethyl-2-hexadecanoyloxy-ethyl ester 
• 1112108-54-9 C₇₀H₁₁₆O₁₅Si₂ 
• 1221152-23-3 C₅₀H₅₈O₁₂ 
• 1221152-26-6 C₅₀H₅₈O₁₂ 
• 109-29-5 15-hexadecanolide 
• 871333-53-8 16-hydroxyhexadecanoic acid 
• 745073-18-1 16-triphenylmethoxy-1-hexadecanol 

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