104-67-6

Basic information

• Product Name: Undecan-4-olide
• Synonyms: PEACH ALDEHYDE;UNDECALACTONE, GAMMA;UNDECAN-4-OLIDE;UNDECANOIC GAMMA-LACTONE;FEMA 3091;GAMMA-UNDECALACTONE;GAMMA-UNDECANOLACTONE;GAMMA-HEPTYL-GAMMA-BUTYROLACTONE
• CAS NO: 104-67-6
• Molecular Formula: C₁₁H₂₀O₂
• Molecular Weight: 184.28
• EINECS: 203-225-4
• Product Categories: Bioactive Small Molecules;Building Blocks;Carbonyl Compounds;Cell Biology;Chemical Synthesis;Lactones;Organic Building Blocks;U;Cosmetics;Food Additive
• Mol File: 104-67-6.mol
• Article Data: 25

Chemical Properties

• Melting Point: 164～166℃
• Boiling Point: 164 °C
• Flash Point: >230 °F
• Appearance: Clear colorless/Liquid
• Density: 0.944 g/mL at 20 °C(lit.)
• Vapor Pressure: 0.00271mmHg at 25°C
• Refractive Index: n20/D 1.451
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Insoluble in water
• Water Solubility: 158mg/L at 20℃
• BRN: 81943
• CAS DataBase Reference: Undecan-4-olide(CAS DataBase Reference)
• NIST Chemistry Reference: Undecan-4-olide(104-67-6)
• EPA Substance Registry System: Undecan-4-olide(104-67-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-52/53
• Safety Statements: 26-36-37/39-36/37-24/25
• WGK Germany: 3
• RTECS: YQ2485000
• TSCA: Yes
• Hazardous Substances Data: 104-67-6(Hazardous Substances Data)

Usage

Description

GAMMA-UNDECALACTONE? is a flavoring ingredient. It is industrially important flavor compounds that are widely distributed in foods, fruits, and beverages and are used in many fruity aromatic foods and cosmetics. It is often used in peach, apricot, pear, maple, coconut, tropical, butterscotch, grenadine and date flavors. It is also a volatile flavor constituent found in low-fat ice cream.

References

https://www.sigmaaldrich.com/catalog/product/aldrich/w309109?lang=en®ion=US https://pubchem.ncbi.nlm.nih.gov/compound/Gamma-undecalactone#section=Top http://www.thegoodscentscompany.com/data/rw1000822.html An, J. U., Y. C. Joo, and D. K. Oh. "New biotransformation process for production of the fragrant compound γ-dodecalactone from 10-hydroxystearate by permeabilized Waltomyces lipofer cells. " Applied & Environmental Microbiology 79.8(2013): 2636-2641.

Chemical Properties

Different sources of media describe the Chemical Properties of 104-67-6 differently. You can refer to the following data:
1. GAMMA-UNDECALACTONE is clear colourless liquid
2. gamma-Undecalactone has a strong, fruity odor suggestive of peach (particularly on dilution). It has a pungent and sweet flavor also similar to peach.

Occurrence

Reported found in hydrolyzed soy protein, butter, peach, apricot and passion fruit. Also reported found in fresh apple, guava fruit, fresh blackberry, heated butter, heated beef fat, ghee, pork fat, yellow passion fruit juice, cooked scented rice, origanum (Spanish) (Coridothymus cap. (L.) Rchb.), mountain papaya, starfruit, plumcot and chicken fat.

Uses

Different sources of media describe the Uses of 104-67-6 differently. You can refer to the following data:
1. Traditionally, the bark and leaves of the peach tree have been used as an anthelmintic, an expectorant, an astringent, and a diuretic, as well as to treat insomnia, cough, and constipation. In the 1970s, peach pits (Laetrile) were a popular but unproved treatment for cancer in other countries. Topically, peach is used to treat minor skin disorders such as burns, abrasions, blisters, scratches, eczema, psoriasis, and warts.
2. 4-Undecanolide is used in the study of primary mutagenicity screening of food additives used in Japan.

Preparation

By the action of sulfuric acid on undecylenic acid; also prepared starting form castor oil; from octanol-1 plus methylacrylate with di-ter-butylperoxide; from heptylethylene oxide and sodiomalonic ester.

Aroma threshold values

Detection: 60 ppb

Taste threshold values

Taste characteristics at 30 ppm: fatty, coconut, creamy, vanilla, nutty, macadamia and peach.

General Description

γ-Undecalactone is a volatile flavor constituent found in low-fat ice cream.

Flammability and Explosibility

Notclassified

InChI:InChI=1/C11H20O2/c1-2-3-4-5-6-7-10-8-9-11(12)13-10/h10H,2-9H2,1H3/t10-/m0/s1

Synthetic route

10-undecenoic acid (112-38-9) → 5-heptyldihydro-2(3H)-furanone (104-67-6)

Conditions	Yield
With 2Zn(2+)*(CH3)3NC2H4OH(1+)*5Cl(1-)=[HOC2H4N(CH3)3]Zn2Cl5 at 130℃; for 8h;	94%
With silver trifluoromethanesulfonate In chlorobenzene at 130℃; for 20h; Inert atmosphere; regioselective reaction;	71%

undec-1-yn-4-ol (22127-86-2) → 5-heptyldihydro-2(3H)-furanone (104-67-6)

Conditions	Yield
With methanesulfonic acid; C21H12F9P*C8H18NO4S2(1-)*Au(1+); 3-chloro-benzenecarboperoxoic acid In 1,2-dichloro-ethane at 20℃; for 5h; Reagent/catalyst;	90%
Multi-step reaction with 2 steps 1.1: n-butyllithium / diethyl ether; hexane / 0.75 h / 0 - 20 °C 1.2: 0 - 20 °C 2.1: C21H12F9P*C8H18NO4S2(1-)*Au(1+); methanesulfonic acid / chloroform-d1 / 20 °C View Scheme

1,4-undecanediol (4272-02-0) → 5-heptyldihydro-2(3H)-furanone (104-67-6)

Conditions	Yield
With aluminum oxide; sodium bromite In acetonitrile for 3h; Ambient temperature;	71%
With 4 A molecular sieve; polymer intercalated (RuCl2(PPh3)3); 4-methylmorpholine N-oxide In acetone at 30℃; for 2h;	79 % Chromat.
Cp*RuCl(Ph2P(CH2)2NH2-κ2-P,N); potassium tert-butylate In acetone at 30℃; for 1h;	95 % Spectr.

4-Hydroxy-undec-2-ynoic acid ethyl ester (114702-12-4) → 5-heptyldihydro-2(3H)-furanone (104-67-6)

Conditions	Yield
With formic acid; tributyl-amine; Pd(OAc)2*3(PPh2) In N,N-dimethyl-formamide at 60℃; for 7h;	64%

1-(cyclopropylidene)octane (50915-95-2) → 5-heptyldihydro-2(3H)-furanone (104-67-6)

Conditions	Yield
With trifluoroacetyl peroxide In dichloromethane at 0℃; for 6h;	87%

octanol (111-87-5) + acrylic acid (79-10-7) → 5-heptyldihydro-2(3H)-furanone (104-67-6)

Conditions	Yield
With di-tert-butyl peroxide at 95 - 180℃; Large scale;	1715 kg
With di-tert-butyl peroxide at 20 - 180℃;	168 g

methyl 4-oxo-dodecanoate (33566-59-5) → 5-heptyldihydro-2(3H)-furanone (104-67-6)

Conditions	Yield
With sodium tetrahydroborate; disodium hydrogenphosphate In methanol 1.) 0 deg C, 5 min, 2.) RT, 24 h;	86%

5-(3E,6-heptadienyl)-dihydro-2(3H)-furanone (81693-14-3) → 5-heptyldihydro-2(3H)-furanone (104-67-6)

Conditions	Yield
With hydrogen; palladium on activated charcoal In hexane at 16℃; for 1h;

non-1-ene (124-11-8) + bromoacetic acid (79-08-3) → 5-heptyldihydro-2(3H)-furanone (104-67-6)

Conditions	Yield
With dibenzoyl peroxide In benzene for 5h; Heating;	58%
With dibenzoyl peroxide In benzene Heating;	58%

1-cyclohexyloxy-undec-1-yn-4-ol → 5-heptyldihydro-2(3H)-furanone (104-67-6)

Conditions	Yield
Stage #1: 1-cyclohexyloxy-undec-1-yn-4-ol With hydrogenchloride In tetrahydrofuran at 20℃; Hydrolysis; Stage #2: With sodium hydride In tetrahydrofuran at 0 - 20℃; Cyclization; Further stages.;

Octanal (124-13-0) → 5-heptyldihydro-2(3H)-furanone (104-67-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 66 percent 2: 64 percent / Bu3N, HCOOH / Pd(OAc)2*3(PPh2) / dimethylformamide / 7 h / 60 °C View Scheme
Multi-step reaction with 2 steps 1: diethyl ether / 1 h / -30 - 20 °C 2: C21H12F9P*C8H18NO4S2(1-)*Au(1+); 3-chloro-benzenecarboperoxoic acid; methanesulfonic acid / 1,2-dichloro-ethane / 5 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1.1: diethyl ether / 1 h / -30 - 20 °C 2.1: n-butyllithium / diethyl ether; hexane / 0.75 h / 0 - 20 °C 2.2: 0 - 20 °C 3.1: C21H12F9P*C8H18NO4S2(1-)*Au(1+); methanesulfonic acid / chloroform-d1 / 20 °C View Scheme

Octanal (124-13-0) + acrylic acid methyl ester (292638-85-8) → 5-heptyldihydro-2(3H)-furanone (104-67-6)

Conditions	Yield
With chloro-trimethyl-silane; tetraethylammonium tosylate In N,N-dimethyl-formamide Ambient temperature; electroreductive crossed hydrocoupling;	77%

β-Propiolactone (57-57-8) + Octanal (124-13-0) → 5-heptyldihydro-2(3H)-furanone (104-67-6)

Conditions	Yield
nickel(II) iodide; samarium diiodide In tetrahydrofuran for 1h; Addition;	83%

1-cyclohexyloxy-undec-1-yn-4-ol → 5-heptyldihydro-2(3H)-furanone (104-67-6) + 4-hydroxy-undecanoic acid cyclohexyl ester

Conditions	Yield
With hydrogenchloride In tetrahydrofuran at 20℃; for 1h; Hydrolysis;

C11H19(2)HO (1396569-87-1) + 3-chloro-benzenecarboperoxoic acid (937-14-4) → C18H24(2)HClO4 (1396571-80-4) + 5-heptyldihydro-2(3H)-furanone (104-67-6)

Conditions	Yield
With methanesulfonic acid; C21H12F9P*C8H18NO4S2(1-)*Au(1+) In chloroform-d1 at 20℃;

5-heptyl-tetrahydro-furan-2-ol (116625-66-2) + 3-chloro-benzenecarboperoxoic acid (937-14-4) → C18H25ClO4 (1396571-72-4) + 5-heptyldihydro-2(3H)-furanone (104-67-6)

Conditions	Yield
With methanesulfonic acid In 1,2-dichloro-ethane at 20℃; for 5h;	A 90 %Spectr. B 10 %Spectr.

2-heptyl-2,3-dihydrofuran (116625-68-4) + 3-chloro-benzenecarboperoxoic acid (937-14-4) → C18H25ClO4 (1396571-72-4) + 5-heptyldihydro-2(3H)-furanone (104-67-6)

Conditions	Yield
With methanesulfonic acid; water In 1,2-dichloro-ethane at 20℃; for 5h; Reagent/catalyst;	A 21 %Spectr. B 33 %Spectr.

5-heptyltetrahydro-2-oxofuran-3-carboxaldehyde → (Z)-4-undecenal (68820-32-6) + (E)-undec-4-enal (68820-35-9) + 5-heptyldihydro-2(3H)-furanone (104-67-6)

Conditions	Yield
With ethyl acetate In tetrahydrofuran; ethanol at 490℃; for 2.5h; Inert atmosphere; optical yield given as %de;	A n/a B n/a C 30%

4-(tert-Butyl-dimethyl-silanyloxy)-undecanoic acid methyl ester → 5-heptyldihydro-2(3H)-furanone (104-67-6)

Conditions	Yield
With tetrabutyl ammonium fluoride	84%

2,3-dichlorotetrahydro-2H-pyran (5631-95-8) → 5-heptyldihydro-2(3H)-furanone (104-67-6)

Conditions

Yield

Multi-step reaction with 7 steps 1: 101 g / diethyl ether; tetrahydrofuran / 4 h / -5 °C 2: Na / diethyl ether / 1.5 h / Heating 3: pyridinium chlorochromate / CH2Cl2 / 1.25 h / Heating 4: 3-(2-ethoxyethyl)-5-(2-hydroxyethyl)-4-methyl-1,3-thiazolium bromide / triethylamine; dioxane / 15 h / 87 °C 5: 1.) NaOH, 2.) NaBH4 / 1.) EtOH-H2O, reflux, 0.5 h, 2.) 2 h 6: 0.5 g / 110 deg C; -> 145 deg C, 20 min; 145 deg C, 10 min 7: H2 / 10percent Pd/C / hexane / 1 h / 16 °C View Scheme

2-Allyl-3-chlor-2H-3,4,5,6-tetrahydropyran (81651-44-7) → 5-heptyldihydro-2(3H)-furanone (104-67-6)

Conditions

Yield

Multi-step reaction with 6 steps 1: Na / diethyl ether / 1.5 h / Heating 2: pyridinium chlorochromate / CH2Cl2 / 1.25 h / Heating 3: 3-(2-ethoxyethyl)-5-(2-hydroxyethyl)-4-methyl-1,3-thiazolium bromide / triethylamine; dioxane / 15 h / 87 °C 4: 1.) NaOH, 2.) NaBH4 / 1.) EtOH-H2O, reflux, 0.5 h, 2.) 2 h 5: 0.5 g / 110 deg C; -> 145 deg C, 20 min; 145 deg C, 10 min 6: H2 / 10percent Pd/C / hexane / 1 h / 16 °C View Scheme

octa-4trans,7-dien-1-ol (81651-45-8) → 5-heptyldihydro-2(3H)-furanone (104-67-6)

Conditions	Yield
Multi-step reaction with 5 steps 1: pyridinium chlorochromate / CH2Cl2 / 1.25 h / Heating 2: 3-(2-ethoxyethyl)-5-(2-hydroxyethyl)-4-methyl-1,3-thiazolium bromide / triethylamine; dioxane / 15 h / 87 °C 3: 1.) NaOH, 2.) NaBH4 / 1.) EtOH-H2O, reflux, 0.5 h, 2.) 2 h 4: 0.5 g / 110 deg C; -> 145 deg C, 20 min; 145 deg C, 10 min 5: H2 / 10percent Pd/C / hexane / 1 h / 16 °C View Scheme

octadiene-4(E),7 al-1 (56053-82-8) → 5-heptyldihydro-2(3H)-furanone (104-67-6)

Conditions	Yield
Multi-step reaction with 4 steps 1: 3-(2-ethoxyethyl)-5-(2-hydroxyethyl)-4-methyl-1,3-thiazolium bromide / triethylamine; dioxane / 15 h / 87 °C 2: 1.) NaOH, 2.) NaBH4 / 1.) EtOH-H2O, reflux, 0.5 h, 2.) 2 h 3: 0.5 g / 110 deg C; -> 145 deg C, 20 min; 145 deg C, 10 min 4: H2 / 10percent Pd/C / hexane / 1 h / 16 °C View Scheme

(E)-hydroxy-7,10-undecadienoic acid (90162-80-4) → 5-heptyldihydro-2(3H)-furanone (104-67-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 0.5 g / 110 deg C; -> 145 deg C, 20 min; 145 deg C, 10 min 2: H2 / 10percent Pd/C / hexane / 1 h / 16 °C View Scheme

ethyl (E)-4-oxoundeca-7,10-dienoate (90162-79-1) → 5-heptyldihydro-2(3H)-furanone (104-67-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: 1.) NaOH, 2.) NaBH4 / 1.) EtOH-H2O, reflux, 0.5 h, 2.) 2 h 2: 0.5 g / 110 deg C; -> 145 deg C, 20 min; 145 deg C, 10 min 3: H2 / 10percent Pd/C / hexane / 1 h / 16 °C View Scheme

Octanal (124-13-0) + diethyl-(2-methoxycarbonyl-ethyl)-methyl-ammonium; iodide (37651-49-3) → 5-heptyldihydro-2(3H)-furanone (104-67-6)

Conditions	Yield
With tetraethylammonium tosylate In N,N-dimethyl-formamide cathodic reduction;	46%

trans-Nonenylmalonsaeure (35329-48-7) → 5-heptyldihydro-2(3H)-furanone (104-67-6)

Conditions	Yield
With sulfuric acid In water for 10h; Heating;

4-Hydroxy-undec-2-ynoic acid ethyl ester (114702-12-4) → 5-heptyl-dihydro-furan-2-one (100591-76-2) + 5-heptyldihydro-2(3H)-furanone (104-67-6)

Conditions	Yield
With formic acid; bis(triphenylphosphine) palladium (Il) acetate; tributyl-amine In N,N-dimethyl-formamide at 60℃; Product distribution; variation excess of formic acid;
With formic acid; tributyl-amine; Pd(OAc)2*(PPh2) In N,N-dimethyl-formamide at 60℃; for 7h; Product distribution; ammount of HCOOH;

Octanal (124-13-0) + t-BuLi → 5-heptyldihydro-2(3H)-furanone (104-67-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 28 percent / LDA / tetrahydrofuran / -78 - 20 °C 2: 87 percent / CF3CO3H / CH2Cl2 / 6 h / 0 °C View Scheme

2-methyl-2-tetradecen-6-one → 5-heptyldihydro-2(3H)-furanone (104-67-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 73 percent / ozone, methanolic NaOH / CH2Cl2 / -70 °C 2: 86 percent / NaBH4, Na2HPO4*12H2O / methanol / 1.) 0 deg C, 5 min, 2.) RT, 24 h View Scheme

5-heptyldihydro-2(3H)-furanone (104-67-6) → 5-heptyl-tetrahydro-furan-2-ol (116625-66-2)

Conditions	Yield
With diisobutylaluminium hydride In toluene at -78℃; for 2h; Reduction;	100%
With diisobutylaluminium hydride
With diisobutylaluminium hydride In toluene
Stage #1: 5-heptyldihydro-2(3H)-furanone With diisobutylaluminium hydride In tetrahydrofuran at -78℃; Stage #2: In water Acidic aq. solution;
Multi-step reaction with 2 steps 1: [(1,3-bis(2,4,6-trimethylphenyl) imidazol-2-ylidene)Fe(CO)4] / toluene / 3 h / 20 °C / Schlenk technique; Inert atmosphere; UV-irradiation 2: hydrogenchloride; water / toluene; tetrahydrofuran / 2 h / 20 °C / Schlenk technique; Inert atmosphere View Scheme

5-heptyldihydro-2(3H)-furanone (104-67-6) → γ-chloroundecanoic acid chloride

Conditions	Yield
With phosphorus pentachloride In benzene at 20℃; for 10h; Chlorination;	100%

5-heptyldihydro-2(3H)-furanone (104-67-6) → undecylenic acid (112-37-8)

Conditions	Yield
With hafnium tetrakis(trifluoromethanesulfonate); palladium on activated carbon; hydrogen In neat (no solvent) at 135℃; under 760.051 Torr; for 12h; Schlenk technique; Glovebox;	99%
With palladium 10% on activated carbon; W(OTf)6; hydrogen at 135℃; under 760.051 Torr; for 12h;	90%
With palladium on activated carbon; W(OTf)6; hydrogen In neat (no solvent) at 135℃; under 760.051 Torr; for 12h;	90%

ethanethiol (75-08-1) + 5-heptyldihydro-2(3H)-furanone (104-67-6) → 4-(ethylthio)undecanoic acid (71057-18-6)

Conditions	Yield
With aluminium trichloride for 37h; Ambient temperature;	91.3%

5-heptyldihydro-2(3H)-furanone (104-67-6) → 1,4-undecanediol (4272-02-0)

Conditions	Yield
With sodium tetrahydroborate In methanol; tert-butyl alcohol Heating;	91%
With diphenylsilane; triphenylphosphine; chloro(1,5-cyclooctadiene)rhodium(I) dimer In tetrahydrofuran at 20℃;	63%
With copper chromite; hydrogen at 210 - 220℃; under 125 - 150 Torr;
With lithium aluminium tetrahydride
With diphenylsilane; triphenylphosphine; chloro(1,5-cyclooctadiene)rhodium(I) dimer In tetrahydrofuran at 20℃; for 72h; Reduction;	63 % Spectr.

5-heptyldihydro-2(3H)-furanone (104-67-6) + formic acid ethyl ester (109-94-4) → 5-heptyltetrahydro-2-oxofuran-3-carboxaldehyde

Conditions	Yield
Stage #1: 5-heptyldihydro-2(3H)-furanone; formic acid ethyl ester With potassium methanolate In diethyl ether at 15 - 20℃; for 3h; Inert atmosphere; Stage #2: With acetic acid In diethyl ether; water at 20℃; for 0.5h; Inert atmosphere;	61%
With sodium hydride In diethyl ether at 20℃; for 3h;

1,1-dibromohexane (58133-26-9) + 5-heptyldihydro-2(3H)-furanone (104-67-6) → 10-Hydroxy-heptadecan-7-one (109586-27-8) + 5-heptyl-2-hexylidene-2,3,4,5-tetrahydrofuran (109586-25-6, 109586-26-7)

Conditions	Yield
With N,N,N,N,-tetramethylethylenediamine; titanium tetrachloride; zinc In tetrahydrofuran at 25℃; for 1.5h;	A 21% B 51%

5-heptyldihydro-2(3H)-furanone (104-67-6) → 4-oxoundecanoic acid (22847-06-9)

Conditions	Yield
Stage #1: 5-heptyldihydro-2(3H)-furanone With water; sodium hydroxide In ethanol at 20℃; for 12h; Inert atmosphere; Stage #2: With Dess-Martin periodane In ethanol; dichloromethane at 20℃; for 5h; Inert atmosphere;	46%
Multi-step reaction with 2 steps 1: NaOH / ethanol 2: NaOCl / aq. phosphate buffer / 20 h / 20 °C / pH 6.6 View Scheme

1,1-Dibromoethane (557-91-5) + 5-heptyldihydro-2(3H)-furanone (104-67-6) → 6-Hydroxy-tridecan-3-one (109586-24-5) + 2-ethylidene-5-heptyl-2,3,4,5-tetrahydrofuran (120387-80-6)

Conditions	Yield
With N,N,N,N,-tetramethylethylenediamine; titanium tetrachloride; zinc In tetrahydrofuran at 25℃; for 2h;	A 41% B 43%

5-heptyldihydro-2(3H)-furanone (104-67-6) → 2-heptyl-2,3-dihydrofuran (116625-68-4)

Conditions	Yield
Stage #1: 5-heptyldihydro-2(3H)-furanone With diisobutylaluminium hydride In dichloromethane at -78℃; for 2h; Inert atmosphere; Stage #2: With methanesulfonyl chloride; triethylamine In tetrahydrofuran at -50℃; for 8h; Reflux;	42%
Multi-step reaction with 3 steps 1: DIBAH 2: BF3*OEt2 3: 58 percent / tBuOOH, Ti(iPrO)4, iPr2NEt / CH2Cl2 / 25 h / 0 °C View Scheme

bis(iodozinc)methane (31729-70-1) + 5-heptyldihydro-2(3H)-furanone (104-67-6) → 2-heptyl-5-methylene-tetrahydro-furan

Conditions	Yield
With N,N,N,N,-tetramethylethylenediamine; titanium chloride In tetrahydrofuran at 25℃; for 4h; methylenation;	28%

5-heptyldihydro-2(3H)-furanone (104-67-6) → 4-hydroxy-undecanoic acid amide

Conditions	Yield
With methanol; ammonia

5-heptyldihydro-2(3H)-furanone (104-67-6) → 1,4-bis-hexanoyloxy-undecane

Conditions	Yield
With copper chromite at 280℃; Hydrogenation.unter Druck und folgenden Verestern mit Capronsaeure in Gegenwart von Naphthalinsulfonsaeure bei 205grad;

Upstream product

• 556-35-4 (-)-4-hydroxy-undeca-6,8,10-triynoic acid 
• 4272-02-0 1,4-undecanediol 
• 74568-02-8 4-hydroxyundecanoic acid 
• 35329-48-7 trans-Nonenylmalonsaeure 
• 120723-28-6 4-(tert-Butyl-dimethyl-silanyloxy)-1-methoxy-1,1-bis-trimethylsilanyl-undecane 
• 114702-12-4 4-Hydroxy-undec-2-ynoic acid ethyl ester 
• 50915-95-2 1-(cyclopropylidene)octane 
• 996-82-7 sodium diethylmalonate 
• 112-38-9 10-undecenoic acid 
• 22127-86-2 undec-1-yn-4-ol 
• 1396569-87-1 C₁₁H₁₉⁽²⁾HO 
• 937-14-4 3-chloro-benzenecarboperoxoic acid 
• 116625-66-2 5-heptyl-tetrahydro-furan-2-ol 
• 116625-68-4 2-heptyl-2,3-dihydrofuran 

Downstream Products

• 4272-02-0 1,4-undecanediol 
• 74568-03-9 (S)-4-Hydroxy-undecanoic acid 
• 74568-06-2 (R)-5-heptyl-dihydrofuran-2-one 
• 95-41-0 2-(n-hexyl)-2-cyclopenten-1-one 
• 87506-18-1 5-hexyl-cyclopent-2-enone 
• 17746-05-3 undecanoyl chloride 
• 112-37-8 undecylenic acid 
• 872-05-9 1-Decene 
• 74568-05-1 (4S)-4-heptyl-γ-butanolide 
• 116625-63-9 2-Benzenesulfonyl-5-heptyl-tetrahydro-furan 
• 116625-67-3 3-Chloro-benzoic acid 5-heptyl-tetrahydro-furan-2-yl ester 
• 116625-62-8 2-heptyl 5-(phenylseleno)tetrahydrofuran 
• 116625-61-7 2-heptyl 5-(phenylthio)tetrahydrofuran 
• 216304-40-4 1-(5-Heptyl-tetrahydro-furan-2-yloxy)-propan-2-one 

Relevant articles and documents

Syntheses of rac- and optically active 2-alkyl-γ-butyrolactones and 2- alkyl-cyclobutanones

γ-Butyrolactones have been produced in good yield from alkylidene cyclopropanes, as racemates or as an enantiomerically enriched mixture of stereoisomers (e.e.>60%) depending upon the method used. Optically active cyclobutanones which are intermediate in the process have been in some cases isolated. We show the limitations of a competitive method previously described and point out its weak step.

Tandem isomerization-lactonization of olefinic fatty acids using the Lewis acidic ionic liquid, choline chloride·2ZnCl2

The tandem isomerization-lactonization of unsaturated fatty acids to their corresponding γ-lactones was carried out for the first time in the presence of a Lewis acidic ionic liquid, choline chloride·2ZnCl 2. The ionic liquid initially catalyzes the stepwise migration of the double bond along the carbon chain toward the carboxyl group at the Δ4 position, which subsequently undergoes lactonization resulting in the formation of γ-lactones. This one step process allows the formation of γ-lactone in good yield with little or no formation of δ-lactones. The studied ionic liquid plays the dual role of solvent as well as catalyst.

Production method of synthesizing gamma-undecalactone synthetic perfume by reactive distillation

The invention belongs to the technical field of fine chemical production, and specifically relates to a production method of synthesizing gamma-undecalactone synthetic perfume by reactive distillation. The method includes the following steps: (a) mixing raw materials to obtain a mixture of ingredients; (b) discharging materials from an octanol elevated tank into a preheater for preheating; (c) pumping octanol into a high-boiling-point feed section of a reaction zone of a reactive distillation column, and pumping the mixture of ingredients into a low-boiling-point feed section of the reaction zone of the reactive distillation column; (d) separating out a crude product of gamma-undecalactone from the bottom of the reactive distillation column; (e) transferring the octanol separated in the step (d) to the preheater through a material pump to continue to participate in the reaction; and (f) further separating and purifying the crude product of gamma-undecalactone separated in the step (d).According to the production method provided by the present invention, a reactive distillation technology is adopted to timely separate by-product water, tert-butanol and low-boiling-point impuritiesproduced by a side reaction from the reaction system, so as to shorten the reaction time, improve the reaction speed and enhance the reaction efficiency.

Efficient synthesis of γ-lactones via gold-catalyzed tandem cycloisomerization/oxidation

A novel Au-catalyzed tandem cycloisomerization/oxidation of homopropargyl alcohols was developed. Various γ-lactones can be accessed readily by utilizing this strategy. Notably, the mechanism of this reaction is distinctively different from the related Ru-catalyzed reactions where the ruthenium vinylidene intermediate was proposed.