delta-Dodecalactone

Reported in EPA TSCA Inventory.

The delta-Dodecalactone, with the CAS registry number 713-95-1, is also known as 5-Hydroxydodecanoic acid delta-lactone. Its EINECS number is 211-932-4. This chemical's molecular formula is C₁₂H₂₂O₂ and molecular weight is 198.30. What's more, its systematic name is 6-Heptyltetrahydro-2H-pyran-2-one. Its classification code is Skin / Eye Irritant. This chemical is stable at common pressure and temperature, and it should be sealed and stored in a cool and dry place. Moreover, it should be protected from oxides. It is mainly used as flavorant. It is used in all kinds of fruit, sweet apricot, honey, cheese, butter chocolate and milk products.

Physical properties of delta-Dodecalactone are: (1)ACD/LogP: 3.488; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.49; (4)ACD/LogD (pH 7.4): 3.49; (5)ACD/BCF (pH 5.5): 263.51; (6)ACD/BCF (pH 7.4): 263.51; (7)ACD/KOC (pH 5.5): 1881.11; (8)ACD/KOC (pH 7.4): 1881.11; (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: 1.448; (14)Molar Refractivity: 57.285 cm³; (15)Molar Volume: 214.101 cm³; (16)Polarizability: 22.71×10^-24cm³; (17)Surface Tension: 30.85 dyne/cm; (18)Density: 0.926 g/cm³; (19)Flash Point: 119.818 °C; (20)Enthalpy of Vaporization: 53.49 kJ/mol; (21)Boiling Point: 295.211 °C at 760 mmHg; (22)Vapour Pressure: 0.002 mmHg at 25°C.

Preparation: this chemical can be prepared by 2-heptyl-cyclopentanone at the ambient temperature. This reaction will need reagents magnesium monoperphthalate hexahydrate, NaHCO₃ and solvents methanol, H₂O with the reaction time of 24 hours. The yield is about 98%.

Uses of delta-Dodecalactone: it can be used to produce dodecane-1,5-diol by heating. It will need reagent NaBH₄ and solvents 2-methyl-propan-2-ol, methanol. The yield is about 89%.

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

You can still convert the following datas into molecular structure:
(1)SMILES: O=C1OC(CCCCCCC)CCC1
(2)Std. InChI: InChI=1S/C12H22O2/c1-2-3-4-5-6-8-11-9-7-10-12(13)14-11/h11H,2-10H2,1H3
(3)Std. InChIKey: QRPLZGZHJABGRS-UHFFFAOYSA-N

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
rabbit	LD50	skin	> 5gm/kg (5000mg/kg)		Food and Cosmetics Toxicology. Vol. 17, Pg. 773, 1979.
rat	LD50	oral	> 5gm/kg (5000mg/kg)		Food and Cosmetics Toxicology. Vol. 17, Pg. 773, 1979.