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

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

Used in Pharmaceutical Industry:
Hexadecanedioic acid is used as a research intermediate for the studies of blood pressure regulations in humans. It plays a crucial role in understanding the mechanisms of blood pressure control and the development of potential therapeutic agents for hypertension.
Used in Drug Development:
Hexadecanedioic acid works in collaboration with SLCO1B1 as a potential therapy for statin. It has been found to enhance the bioavailability and efficacy of statin drugs, which are commonly used to lower cholesterol levels and reduce the risk of cardiovascular diseases.

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 
• 2550-52-9 cyclohexadecanone 
• 544-76-3 Hexadecane 
• 65119-97-3 heptadec-16-enoic acid 
• 19102-90-0 dimethyl hexadecanedioate 
• 7735-42-4 1,16-hexadecanediol 
• 57-57-8 β-Propiolactone 
• 23708-54-5 1,10-Decandiylbis(magnesiumbromid) 
• 88739-44-0 1-(tert-Butyl-dimethyl-silanyloxy)-cyclooctyl-hydroperoxide 

Downstream Products

• 502-72-7 cyclopentadecanone 
• 15786-31-9 diethyl hexadecanedioate 
• 18017-66-8 hexadecanedioic acid monoethyl ester 
• 7735-42-4 1,16-hexadecanediol 
• 443770-14-7 hexadecanedioic acid mono-(2-oxo-2-phenyl-ethyl) ester 
• 177334-75-7 15-[(4-Benzyloxycarbonylamino-butyl)-(3-benzyloxycarbonylamino-propyl)-carbamoyl]-pentadecanoic acid 

Relevant articles and documents

Preparation method of long-chain diacid

The invention provides a preparation method of long-chain diacid, which comprises the following steps of: (S1) carrying out an addition reaction on olefine acid or an ester derivative thereof serving as a raw material and liquid bromine to obtain dibromo carboxylic acid or an ester derivative thereof; (S2) carrying out an elimination reaction on the dibromo carboxylic acid or ester derivative thereof under the action of sodium amide to obtain alkynyl-terminated carboxylic acid or an ester derivative thereof; (S3) carrying out an addition reaction on the alkynyl-terminated carboxylic acid or the ester derivative thereof and diborane to obtain borane or boric acid containing carboxyl or ester group; and (S4) oxidizing the borane or boric acid to obtain long-chain diacid. According to the invention, olefine acid is used as a raw material, is easily available in source and low in price, so that the production cost of the product is very low; and meanwhile, the raw materials used in the synthesis process do not contain precious metals or other expensive reagents, so that the synthesis process is suitable for industrial amplification production, and the defect that the method in the prior art is not environment-friendly, not suitable for industrial production and high in preparation cost is overcome.

Preparation method of long-chain alkyl diacid

The invention relates to a preparation method of long-chain alkyl diacid, belonging to the technical field of organic synthesis. The method is characterized in that long-chain alkyl diacid is prepared by hydrolyzing a long-chain alkyl acid derivative serving as a starting raw material under an acidic condition. According to the invention, a novel synthesis route is adopted, raw material cost is reduced, and the synthesis method has the characteristics of mild reaction conditions, simple process operation, low production cost and the like, and shows good application prospects. The long-chain alkyl diacid serving as an intermediate for medicine synthesis has very high application value and very high economic value.

Preparation method of long-chain alkyl diacid mono-tert-butyl ester

The invention relates to a preparation method of long-chain alkyl diacid mono-tert-butyl ester, belonging to the technical field of organic synthesis. According to the invention, long-chain alkyl diacid is used as an initial raw material and reacts with oxalyl chloride to generate long-chain monoacyl chloride, and the long-chain monoacyl chloride and tert-butyl alcohol are subjected to an esterification reaction to generate the long-chain alkyl diacid mono-tert-butyl ester. According to the invention, a novel synthesis route is adopted, and raw material cost is reduced; and the method has the characteristics of mild reaction conditions, simple process operation, high product purity, high production efficiency and the like, and has good application prospects.

cis/trans-Ozonides of Cycloolefins

Ozonolyses in pentane of the unsubstituted cycloolefins having eleven-, twelve-, fourteen- and sixteen-membered rings (1b-e) and of cyclohexadecen-8-one (12) gave the corresponding cis- (2b-e; cis-15a) and trans-ozonides (3b-e; trans-15a), whereas cyclodecene (1a) gave only the corresponding cis-ozonide (2a).Ozonolyses on polyethylene of the dimethyl-substituted cycloolefins bearing fourteen- and sixteen-membered rings (7b,c) also afforded cis- and trans-isomeric ozonides (8, 9), whereas from the twelve-membered ring (7a) only the corresponding cis-ozonide (8a) was formed. - Keywords: Ozonides; Cycloolefins

One-step Synthesis of Long-chain Aliphatic α,ω-Dicarboxylic Acids Utilizing the Copper-catalyzed Reaction of β-Propiolactone with α,ω-Di-Grignard Reagents

Copper-catalyzed reaction of β-propiolactone with α,ω-di-Grignard reagents, followed by esterification gave six-carbon homologated α,ω-dicarboxylic acid esters in good yields.

Free Acids in Lac Resin

Lac resin has been found to contain 10.70 percent free fatty and 2.7 percent free aldehydic terpenic acids.The free fatty acids are composed of (i) saturated and unsaturated straight, chain lengths of C14, C16 and C18 (ii) 6-ketotetradecanoic , (iii) 6-hydroxytetradecanoic (butolic), (iv) 16-hydroxyhexadecanoic, (v) 16-hydroxyhexadec-cis-9-enoic, (vi) threo-9,10-dihydroxy of C14 and C16 chain lengths and (vii) threo-9,10,16-trihydroxy hexadecanoic (aleuritic) acids, while the terpenic acids constitute a mixture of jalaric, laccijalaric and a new aldehydic acid (C15H18O3).