505-54-4

Basic information

• Product Name: HEXADECANEDIOIC ACID
• Synonyms: THAPSIC ACID;Hexadecane-1,16-dioic acid;n-Tetradecane-omega,omega'-dicarboxylic acid;DICARBOXYLIC ACID C16;HEXADECANE DIACID;HEXADECANEDIOIC ACID;1,16-HEXADECANEDIOIC ACID;1,14-TETRADECANEDICARBOXYLIC ACID
• CAS NO: 505-54-4
• Molecular Formula: C₁₆H₃₀O₄
• Molecular Weight: 286.41
• EINECS: 208-013-5
• Product Categories: alpha,omega-Alkanedicarboxylic Acids;alpha,omega-Bifunctional Alkanes;Monofunctional & alpha,omega-Bifunctional Alkanes;canedioic acid;1,16-HEXADECANEDIOIC ACID
• Mol File: 505-54-4.mol
• Article Data: 9

Chemical Properties

• Melting Point: 120-123 °C(lit.)
• Boiling Point: 451.08°C (rough estimate)
• Flash Point: 244.6 °C
• Appearance: white powder
• Density: 1.0351 (rough estimate)
• Vapor Pressure: 1.22E-09mmHg at 25°C
• Refractive Index: 1.4485 (estimate)
• Storage Temp.: 2-8°C
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 4.48±0.10(Predicted)
• Water Solubility: 5.098mg/L at 20℃
• Stability: Stable. Incompatible with bases, oxidizing agents, reducing agents. Combustible.
• BRN: 1792831
• CAS DataBase Reference: HEXADECANEDIOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: HEXADECANEDIOIC ACID(505-54-4)
• EPA Substance Registry System: HEXADECANEDIOIC ACID(505-54-4)

Safety Data

• Statements: 36/37/38
• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 505-54-4(Hazardous Substances Data)

Usage

Uses

Hexadecanedioic Acid is a useful research intermediate for the studies of blood pressure regulations in humans. Hexadecandedioate works in collaboration with SLCO1B1 as a potential therapy for statin.

Chemical Properties

white powder

Definition

ChEBI: An alpha,omega-dicarboxylic acid that is the 1,14-dicarboxy derivative of tetradecane.

Purification Methods

Crystallise thaspic acid from EtOH, ethyl acetate or *C6H6. [Beilstein 2 IV 2162.]

InChI:InChI=1/C16H30O4/c17-15(18)13-11-9-7-5-3-1-2-4-6-8-10-12-14-16(19)20/h1-14H2,(H,17,18)(H,19,20)/p-2

Synthetic route

C24H38O8 (81393-29-5) → thapsic acid (505-54-4)

Conditions	Yield
With hydrogenchloride In water Heating;	95%

hexadec-8t-enedioic acid (121626-90-2) → thapsic acid (505-54-4)

Conditions	Yield
With methanol; nickel Hydrogenation;
With acetic acid; platinum Hydrogenation;

1,12-dibromododecane (3344-70-5) + sodium diethylmalonate (996-82-7) → thapsic acid (505-54-4)

Conditions	Yield
Durch Verseifen und Erhitzen der erhaltenen Tetracarbonsaeure;

16-hydroxyhexadecanoic acid (506-13-8) → thapsic acid (505-54-4)

Conditions	Yield
With chromium(VI) oxide; acetic acid
With chromium(VI) oxide
With chromium(VI) oxide; sulfuric acid In acetone

hexadecanediamide (89790-15-8) → thapsic acid (505-54-4)

Conditions	Yield
With potassium hydroxide

5,12-dioxo-hexadecanedioic acid (408311-05-7) → thapsic acid (505-54-4)

Conditions	Yield
With potassium hydroxide; hydrazine hydrate; diethylene glycol
With hydrogenchloride; amalgamated zinc; acetic acid

7-semicarbazono-hexadecanedioic acid (109155-87-5) → thapsic acid (505-54-4)

Conditions	Yield
With potassium hydroxide; hydrazine hydrate; diethylene glycol

cyclohexadecanone (2550-52-9) → thapsic acid (505-54-4)

Conditions	Yield
With chromium(VI) oxide; acetic acid

5,12-dioxo-hexadecanedioic acid bis-methylamide → thapsic acid (505-54-4)

Conditions	Yield
With sodium; hydrazine hydrate; ethylene glycol

Hexadecane (544-76-3) → thapsic acid (505-54-4)

Conditions	Yield
(microbiological transformation);

azelaic acid monoethyl ester (1593-55-1) + 9-acetoxy nonanoic acid (30993-88-5) → thapsic acid (505-54-4)

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

heptadec-16-enoic acid (65119-97-3) → thapsic acid (505-54-4)

Conditions	Yield
With potassium permanganate In acetone

dimethyl hexadecanedioate (19102-90-0) → thapsic acid (505-54-4)

Conditions	Yield
(saponification);

1,16-hexadecanediol (7735-42-4) → thapsic acid (505-54-4)

Conditions	Yield
With potassium permanganate In water; acetone at 70℃;

5-Oxohexadecanedioic Acid (3974-28-5) → thapsic acid (505-54-4)

Conditions	Yield
(i) NaOH, N2H4*H2O, (ii) (heating); Multistep reaction;

6-Oxo-hexadecan-disaeure (93158-51-1) → thapsic acid (505-54-4)

Conditions	Yield
With potassium hydroxide; hydrazine hydrate In diethylene glycol

4-Oxo-tetradecan-dicarbonsaeure-(1,14)-diethylester (102376-23-8) → thapsic acid (505-54-4)

Conditions	Yield
(i) N2H4*H2O, HOCH2CH2OCH2CH2OH, (ii) KOH, (thermolysis); Multistep reaction;

17-Phenyl-stearinsaeure (3839-45-0) → thapsic acid (505-54-4)

Conditions	Yield
With chromium(VI) oxide In acetic acid at 100℃;

4-Oxo-hexadecandisaeure (17204-92-1) → thapsic acid (505-54-4)

Conditions	Yield
(i) KOH, N(CH2CH2OH)3, (ii) N2H4*H2O, (iii) KOH; Multistep reaction;

β-Propiolactone (57-57-8) + 1,10-Decandiylbis(magnesiumbromid) (23708-54-5) → thapsic acid (505-54-4)

Conditions	Yield
With dilithium tetrachlorocuprate In tetrahydrofuran at 0℃; for 3h;

1-(tert-Butyl-dimethyl-silanyloxy)-cyclooctyl-hydroperoxide (88739-44-0) → thapsic acid (505-54-4)

Conditions	Yield
With sulfuric acid; water; iron(II) sulfate 1.) 0 deg C, methanol 2.) RT; Yield given. Multistep reaction;

2,3,19-Trioxabicyclo<14.2.1>nonadecane → thapsic acid (505-54-4) + 15-formylpentadecanoic acid (69275-06-5)

Conditions	Yield
In benzene-d6 at 80℃; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

1-methyl-4-nitrosobenzene (623-11-0) + 6-[5-(5-carboxy-[2]thienylmethyl)-[2]thienyl]-hexanoic acid (857979-06-7) + nickel-aluminium-alloy → thapsic acid (505-54-4)

2-thiophenebutyric acid (4653-11-6) + aqueous sodium carbonate-solution + Raney nickel → Octanoic acid (124-07-2) + thapsic acid (505-54-4)

7-oxo-tetradecane-dicarboxylic acid-(1.14) → thapsic acid (505-54-4)

Conditions	Yield
With hydrogenchloride; amalgamated zinc unter Durchleiten von Chlorwasserstoff;

1,14-tetradecanediol (19812-64-7) + carbon monoxide → thapsic acid (505-54-4)

Conditions	Yield
With iodine; tetracarbonyl nickel at 260℃; under 147102 Torr;

zibetan → thapsic acid (505-54-4)

Conditions	Yield
With permanganate(VII) ion; benzene

(E)-tert-butyl (cyclooct-1-en-1-yloxy)dimethylsilane (67788-03-8) → thapsic acid (505-54-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: H2O2 / trifluoroacetic acid 2: 1.)FeSO4 2.) H2O, H2SO4 / 1.) 0 deg C, methanol 2.) RT View Scheme

thapsic acid (505-54-4) → 1,16-hexadecanediol (7735-42-4)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran for 4h; Reflux;	96%
With lithium aluminium tetrahydride In tetrahydrofuran for 24h; Reduction; Heating;	92%
With lithium aluminium tetrahydride In tetrahydrofuran Ambient temperature;	84%

thapsic acid (505-54-4) → 1,16-hexadecanedioyl dichloride (34959-19-8)

Conditions	Yield
With thionyl chloride In benzene for 2h; Heating;	95%
With thionyl chloride for 3h; Heating;
With thionyl chloride for 1h; Heating;

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + thapsic acid (505-54-4) → hexadecanedioic acid bis-(2,5-dioxopyrrolidin-1-yl)ester (191091-30-2)

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

thapsic acid (505-54-4) + benzyl alcohol (100-51-6) → dibenzyl hexadecanedioate

Conditions	Yield
With toluene-4-sulfonic acid In toluene at 120℃; for 24h;	95%
With toluene-4-sulfonic acid In toluene for 8h; Heating / reflux;

thapsic acid (505-54-4) + N1-(tert-butoxycarbonyl)-N2-[3-(1-trityl-1H-imidazol-4-yl)propyl]guanidine (1146622-60-7) → N1,N16-bis{(tert-butoxycarbonylamino)[3-(1-trityl-1H-imidazol-4-yl)propylamino]methylene}hexadecanediamide (1356946-87-6)

Conditions	Yield
Stage #1: thapsic acid With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine In dichloromethane for 0.25h; Inert atmosphere; Stage #2: N1-(tert-butoxycarbonyl)-N2-[3-(1-trityl-1H-imidazol-4-yl)propyl]guanidine In dichloromethane at 20℃; Inert atmosphere;	88%

thapsic acid (505-54-4) + glycerol (56-81-5) → hexadecandioic acid bis(2,3-dihydroxypropyl)ester

Conditions	Yield
With mesoporous silica HMS2-SO3H at 110℃; for 6h; Product distribution; Further Variations:; Reagents; reaction times;	86%

thapsic acid (505-54-4) + acotinine (302-27-2) → C48H73NO13

Conditions	Yield
With 2,3,5-trimethyl-pyridine In tetrahydrofuran at 70℃; for 5h;	85.5%

thapsic acid (505-54-4) + toluene-4-sulfonic acid (104-15-4) → 1,14-tetradecyldiammonium ditosylate

Conditions	Yield
Stage #1: thapsic acid With sodium azide; sulfuric acid In chloroform at 50℃; for 2h; Schmidt Reaction; Stage #2: toluene-4-sulfonic acid	73%

thapsic acid (505-54-4) + 11-amino-N-(strychnin-2-yl)undecanoic acid amide → N1,N16-Bis[N-(strychnine-2-yl)undecanoic Acid Amide-11-yl]hexadecanediamide

Conditions	Yield
Stage #1: thapsic acid With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane for 0.166667h; Inert atmosphere; Cooling with ice; Stage #2: 11-amino-N-(strychnin-2-yl)undecanoic acid amide In dichloromethane at 20℃; for 14h; Inert atmosphere; Cooling with ice;	71%

methanol (67-56-1) + thapsic acid (505-54-4) → dimethyl hexadecanedioate (19102-90-0)

Conditions	Yield
With hydrogenchloride In water at 20℃; for 4h;	69%
With thionyl chloride at 20℃; for 6h;

ethanol (64-17-5) + thapsic acid (505-54-4) → diethyl hexadecanedioate (15786-31-9) + hexadecanedioic acid monoethyl ester (18017-66-8)

Conditions	Yield
With sulfuric acid In cyclohexane for 48h;	A n/a B 68%

thapsic acid (505-54-4) + α-bromoacetophenone (70-11-1) → hexadecanedioic acid mono-(2-oxo-2-phenyl-ethyl) ester (443770-14-7)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 25℃; for 24h;	65%

vinyl acetate (108-05-4) + thapsic acid (505-54-4) → divinyl hexadecanedioate (160907-11-9)

Conditions	Yield
With sulfuric acid; mercury(II) diacetate for 4h; Reflux; Inert atmosphere;	64%

4'-demethyl-4-deoxypodophyllotoxin (3590-93-0, 85440-15-9, 123287-54-7, 123287-57-0) + thapsic acid (505-54-4) → Hexadecanedioic acid mono-[2,6-dimethoxy-4-((5R,5aR,8aR)-6-oxo-5,5a,6,8,8a,9-hexahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl)-phenyl] ester

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0℃; for 2h;	63%

thapsic acid (505-54-4) + <3-<<4-(carboxyamino)butyl>amino>propyl>carbamic acid, dibenzyl ester (89965-56-0) → 15-[(4-Benzyloxycarbonylamino-butyl)-(3-benzyloxycarbonylamino-propyl)-carbamoyl]-pentadecanoic acid (177334-75-7)

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 24h;	62%

thapsic acid (505-54-4) + tert-butyl 5-[3-(2-tert-butoxycarbonylguanidino)propyl]thiazol-2-yl-carbamate (1151467-62-7) → N1,N16-bis((tert-butoxycarbonylamino){3-[2-(tert-butoxycarbonyl)aminothiazol-5-yl]propylamino}methylene)hexadecanediamide (1356946-78-5)

Conditions	Yield
Stage #1: thapsic acid With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine In dichloromethane for 0.25h; Inert atmosphere; Stage #2: tert-butyl 5-[3-(2-tert-butoxycarbonylguanidino)propyl]thiazol-2-yl-carbamate In dichloromethane at 20℃; Inert atmosphere;	62%

thapsic acid (505-54-4) + metronidazole (443-48-1) → 16-(2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethoxy)-16-oxohexadecanoic acid (848046-35-5)

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 12h;	60%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dimethyl sulfoxide at 40℃; for 24h;	57.4%
Stage #1: thapsic acid With dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; for 2h; Stage #2: metronidazole With dmap In tetrahydrofuran	37.2%
Stage #1: thapsic acid With dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; for 2h; Stage #2: metronidazole With dmap In tetrahydrofuran	37.2%

thapsic acid (505-54-4) + N-trityl-N,N'-bis-[3-(trityl-amino)-propyl]-butane-1,4-diamine (213403-58-8) → C150H162N8O2

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate In N,N-dimethyl-formamide at 25℃; for 24h;	57%

thapsic acid (505-54-4) + benzyl bromide (100-39-0) → 16-(benzyloxy)-16-oxohexadecanoic acid (146004-98-0)

Conditions	Yield
With sodium carbonate In 2-methyltetrahydrofuran; water at 75℃; for 22h;	55.6%
With tetrabutylammomium bromide; potassium hydroxide In methanol Inert atmosphere;	42%

thapsic acid (505-54-4) + ciprofloxacin (85721-33-1)

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 4h;	55%

+ tert-butyl 5-[3-(2-tert-butoxycarbonylguanidino)propyl]-4-methylthiazol-2-yl-carbamate → N1,N16-bis((tert-butoxycarbonylamino){3-[2-(tert-butoxycarbonyl)amino-4-methylthiazol-5-yl]propylamino}methylene)hexadecanediamide (1356946-70-7)

Conditions	Yield
Stage #1: thapsic acid With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine In dichloromethane for 0.25h; Inert atmosphere; Stage #2: tert-butyl 5-[3-(2-tert-butoxycarbonylguanidino)propyl]-4-methylthiazol-2-yl-carbamate In dichloromethane at 20℃; Inert atmosphere;	54%

thapsic acid (505-54-4) + Dideoxyinosine (69655-05-6) → 2',3'-dideoxy-5'-hydrogen hexadecanedioate inosine (879015-25-5)

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran at 20℃;	50.5%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran at 20℃;	50.5%

thapsic acid (505-54-4) + template CS diol (110224-49-2) → C67H74O4 (124461-68-3)

Conditions	Yield
With dmap; 4-(dimethylamino)pyridine hydrochloride; dicyclohexyl-carbodiimide In chloroform for 14h; Heating;	50%

thapsic acid (505-54-4) + benzyl chloride (100-44-7) → 16-(benzyloxy)-16-oxohexadecanoic acid (146004-98-0)

Conditions	Yield
With potassium carbonate In tetrahydrofuran; water at 80℃; for 40h;	50%

thapsic acid (505-54-4) + N,N-dimethylformamide di-tert-butyl acetal (36805-97-7) → hexadecanedioic acid mono-tert-butyl ester (843666-27-3)

Conditions	Yield
In toluene Reflux;	49%
In toluene Reflux;	47.6%
Stage #1: thapsic acid; N,N-dimethylformamide di-tert-butyl acetal In toluene at 50℃; Stage #2: With ethyl acetate In dichloromethane for 0.25h;	33%

thapsic acid (505-54-4) + hydroxytyrosol (10597-60-1) → bis(3,4-dihydroxyphenethyl) hexadecanedioate

Conditions	Yield
With toluene-4-sulfonic acid In tetrahydrofuran at 75℃;	48%

thapsic acid (505-54-4) + butyl-α-D-glucopyranoside (5391-18-4, 25320-93-8, 39824-09-4, 95531-15-0, 143289-25-2, 146453-36-3, 148347-27-7) → butyl 6-O-hexadecanedioyl-α-D-glucopyranoside

Conditions	Yield
pig pancreatic lipase In acetone at 45℃; for 72h;	47%

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + thapsic acid (505-54-4) → ω-carboxypentanedecanoic acid monosuccinimidyl ester

Conditions	Yield
With dicyclohexyl-carbodiimide In 1,4-dioxane; ethyl acetate at 20℃; for 12h;	45%
With dmap; dicyclohexyl-carbodiimide In tetrahydrofuran for 0.5h;	41%

7-[4-(2-chloroacetyl) piperazin-1-yl]-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid + thapsic acid (505-54-4) → C54H66F2N6O12 (1350462-77-9)

Conditions	Yield
Stage #1: thapsic acid With caesium carbonate In N,N-dimethyl-formamide at 50℃; for 1h; Stage #2: 7-[4-(2-chloroacetyl) piperazin-1-yl]-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid With tetra-(n-butyl)ammonium iodide In N,N-dimethyl-formamide at 50℃; for 72h;	41%

Upstream product

• 121626-90-2 hexadec-8t-enedioic acid 
• 3344-70-5 1,12-dibromododecane 
• 996-82-7 sodium diethylmalonate 
• 506-13-8 16-hydroxyhexadecanoic acid 
• 89790-15-8 hexadecanediamide 
• 408311-05-7 5,12-dioxo-hexadecanedioic acid 
• 109155-87-5 7-semicarbazono-hexadecanedioic acid 
• 2550-52-9 cyclohexadecanone 
• 1593-55-1 azelaic acid monoethyl ester 
• 30993-88-5 9-acetoxy nonanoic acid 
• 93158-51-1 6-Oxo-hexadecan-disaeure 
• 102376-23-8 4-Oxo-tetradecan-dicarbonsaeure-(1,14)-diethylester 
• 19812-64-7 1,14-tetradecanediol 
• 5675-51-4 1,12-dodecandiol 

Downstream Products

• 502-72-7 cyclopentadecanone 
• 7735-42-4 1,16-hexadecanediol 
• 500711-80-8 mono (2,4,6-triiodophenyl) hexadecanedioate 
• 146004-98-0 16-(benzyloxy)-16-oxohexadecanoic acid 
• 1379676-98-8 [N-(15-carboxypentadecanoyl)isoleucyl]phenylalanylamide 
• 1379677-17-4 C₄₆H₇₂N₆O₆ 
• 1379677-01-6 C₃₉H₆₁N₅O₈ 
• 629-59-4 tetradecane 
• 871-70-5 octadecanedioic acid 
• 443770-21-6 15-{[4-(trityl-amino)-butyl]-[3-(trityl-amino)-propyl]-carbamoyl}-pentadecanoic acid 2-oxo-2-phenyl-ethyl ester 
• 443770-19-2 15-{(4-dibenzylamino-butyl)-[3-(trityl-amino)-propyl]-carbamoyl}-pentadecanoic acid 2-oxo-2-phenyl-ethyl ester 
• 443770-22-7 15-{[4-(trityl-amino)-butyl]-[3-(trityl-amino)-propyl]-carbamoyl}-pentadecanoic acid 
• 443770-20-5 15-{(4-dibenzylamino-butyl)-[3-(trityl-amino)-propyl]-carbamoyl}-pentadecanoic acid 

Relevant articles and documents

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