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Undecan-4-olide

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Name

Undecan-4-olide

EINECS 203-225-4
CAS No. 104-67-6 Density 0.9425 g/cm3
PSA 26.30000 LogP 3.05250
Solubility 158mg/L at 20℃ Melting Point 164~166℃
Formula C11H20O2 Boiling Point 286 °C at 760 mmHg
Molecular Weight 184.279 Flash Point 112.7 °C
Transport Information N/A Appearance Colourless oily liquid
Safety 26-36/37/39 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 104-67-6 (Undecan-4-olide) Hazard Symbols IrritantXi
Synonyms

Undecanoicacid, 4-hydroxy-, g-lactone(6CI,7CI);4-Hydroxyundecanoic acid lactone;4-Undecanolide;5-Heptyldihydro-2(3H)-furanone;5-Heptyltetrahydro-2-furanone;NSC 406421;NSC46118;NSC 76413;Neutralizing agent 350120-1;Peach lactone;Peche Pure;Persicol;g-(n-Heptyl)-g-butyrolactone;g-Heptyl-g-butyrolactone;g-Heptylbutyrolactone;g-Undecalactone;g-Undecanolactone;g-Undecanolide;g-n-Heptylbutyrolactone;

Article Data 36

Undecan-4-olide Synthetic route

112-38-9

10-undecenoic acid

104-67-6

5-heptyldihydro-2(3H)-furanone

Conditions
ConditionsYield
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%
22127-86-2

undec-1-yn-4-ol

104-67-6

5-heptyldihydro-2(3H)-furanone

Conditions
ConditionsYield
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
4272-02-0

1,4-undecanediol

104-67-6

5-heptyldihydro-2(3H)-furanone

Conditions
ConditionsYield
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.
114702-12-4

4-Hydroxy-undec-2-ynoic acid ethyl ester

104-67-6

5-heptyldihydro-2(3H)-furanone

Conditions
ConditionsYield
With formic acid; tributyl-amine; Pd(OAc)2*3(PPh2) In N,N-dimethyl-formamide at 60℃; for 7h;64%
50915-95-2

1-(cyclopropylidene)octane

104-67-6

5-heptyldihydro-2(3H)-furanone

Conditions
ConditionsYield
With trifluoroacetyl peroxide In dichloromethane at 0℃; for 6h;87%
111-87-5

octanol

79-10-7

acrylic acid

104-67-6

5-heptyldihydro-2(3H)-furanone

Conditions
ConditionsYield
With di-tert-butyl peroxide at 95 - 180℃; Large scale;1715 kg
With di-tert-butyl peroxide at 20 - 180℃;168 g
33566-59-5

methyl 4-oxo-dodecanoate

104-67-6

5-heptyldihydro-2(3H)-furanone

Conditions
ConditionsYield
With sodium tetrahydroborate; disodium hydrogenphosphate In methanol 1.) 0 deg C, 5 min, 2.) RT, 24 h;86%
81693-14-3

5-(3E,6-heptadienyl)-dihydro-2(3H)-furanone

104-67-6

5-heptyldihydro-2(3H)-furanone

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In hexane at 16℃; for 1h;
124-11-8

non-1-ene

79-08-3

bromoacetic acid

104-67-6

5-heptyldihydro-2(3H)-furanone

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

1-cyclohexyloxy-undec-1-yn-4-ol

104-67-6

5-heptyldihydro-2(3H)-furanone

Conditions
ConditionsYield
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.;

Undecan-4-olide Consensus Reports

Reported in EPA TSCA Inventory.

Undecan-4-olide Specification

The CAS registry number of Undecan-4-olide is 104-67-6. Its EINECS registry number is 203-225-4. The IUPAC name is 5-heptyloxolan-2-one. In addition, the molecular formula is C11H20O2 and the molecular weight is 184.28. It is also called dihydro-5-heptyl-2(3H)-furanone. What's more, it is a kind of clear colourless liquid. It should be stored in a cool and dry place.

Physical properties about this chemical are: (1)ACD/LogP: 2.92; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.92; (4)ACD/LogD (pH 7.4): 2.92; (5)ACD/BCF (pH 5.5): 96.85; (6)ACD/BCF (pH 7.4): 96.85; (7)ACD/KOC (pH 5.5): 918.85; (8)ACD/KOC (pH 7.4): 918.85; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 6; (12)Polar Surface Area: 26.3 Å2; (13)Index of Refraction: 1.449; (14)Molar Refractivity: 52.67 cm3; (15)Molar Volume: 196.3 cm3; (16)Polarizability: 20.88 ×10-24cm3; (17)Surface Tension: 31.3 dyne/cm; (18)Density: 0.938 g/cm3; (19)Flash Point: 112.7 °C; (20)Enthalpy of Vaporization: 52.51 kJ/mol; (21)Boiling Point: 286 °C at 760 mmHg; (22)Vapour Pressure: 0.00271 mmHg at 25°C.

Preparation of Undecan-4-olide: it can be prepared by undecenoic acid in the presence of sulfuric acid through esterification reaction. And then after a series of separation, washing and distillation you can get the desired product. In addition, it can be prepared by cyclopropylideneoctane. This reaction will need reagent CF3CO3H and solvent CH2Cl2. The reaction time is 6 hours at reaction temperature of 0 °C. The yield is about 87%.

Undecan-4-olide can be prepared by cyclopropylideneoctane

Uses of Undecan-4-olide: it is used as a food flavor. And it can be used to get 5-heptyl-tetrahydro-furan-2-ol. This reaction will need reagent i-Bu2AlH and solvent toluene. The reaction time is 2 hours at reaction temperature of -78 °C. The yield is about 100%.

Undecan-4-olide can be used to get 5-heptyl-tetrahydro-furan-2-ol

When you are using this chemical, please be cautious about it as the following:
It is irritating to eyes, respiratory system and skin. When you are using it, wear suitable protective clothing, gloves and eye/face protection. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C1OC(CCCCCCC)CC1
(2)InChI: InChI=1/C11H20O2/c1-2-3-4-5-6-7-10-8-9-11(12)13-10/h10H,2-9H2,1H3
(3)InChIKey: PHXATPHONSXBIL-UHFFFAOYAL

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
rat LD50 oral 18500mg/kg (18500mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

SKIN AND APPENDAGES (SKIN): HAIR: OTHER
Food and Cosmetics Toxicology. Vol. 2, Pg. 327, 1964.

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