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Odor Properties & Molecular Visualization

delta-Lactones
&
Molecular Structures 

gamma-Lactones and delta-lactones are important flavor and aroma constituents in many natural products. Although both chiral enantiomeric forms occur in nature, the "R" chiral forms tend to be predominant (especially as the alkyl chain length increases). In constructiing molecular models, we will show only the "R-" enantiomers (as shown below for delta-decalactone as pictured by the Accelrys Discovery Studio Visualizer with the chiral monitor turned on).

 

 

delta-Hexalactone or 5-methylpentanolide...C6H10O2

..........................................
is a relatively weak flavor chemical that occurs in products such as Butter, Coconut, Raspberry, Strawberry, Tea.. The odor is described as coumarinic with coconut, cream, and chocolate notes.

Odor Detection Threshold = NA
Coumarinic odor; coconut, cream, chocolate notes.

delta-Octalactone or 5-propylpentanolide...C8H14O2

..............................
occurs in products such as Apricot, Blue Cheese, Burley Tobacco, Butter, Cheddar Cheese, Coconut, Cream, Pineapple, Raspberry, Strawberry, Yogurt. Mosciano, et. al. report that this material has a "sweet, creamy, fatty with tropical and dairy nuances" odor and a "sweet fatty coconut, with creamy dairy nuances" odor at 10 ppm.

Odor Detection Threshold (in water) = 400 ppb
Coumarin-like, sweet odor and taste; creamy note

delta-Nonalactone or 5-butylpentanolide...C9H16O2

..........................

occurs in products such as Butter, Cooked Beef, Cooked Pork, Milk, Whiskey, Wine.. Mosciano, et. al. (1995) describe the odor as "sweet, lactonic and coconut with creamy, dairy, waxy nuances" and taste (at 10 ppm) as "creamy, coconut, lactonic, sweet and dairy-like with milky nuances".

Odor Detection Threshold (in water) = 400 ppb
Sweet, oily-fatty, coconut odor; fruity, dairy-cream-like taste

delta-Decalactone or 5-pentylpentanolide...C10H18O2

...........................
occurs in products such as Apricot, Blue Cheese, Burley Tobacco, Butter, Coconut, Mango, Peach, Raspberry, Rum, Strawberry, Tea. The odor is sweet, creamy, milky, peach, nut; peach, buttery in dilution.

Odor Detection Threshold (in water) = 100 ppb
Sweet, creamy, milky, peach, nut; peach, buttery in dilution

delta-Undecalactone or 5-hexylpentanolide...C11H20O2

..........................
occurs in products such as Butter, Coconut, Cream, Milk. Mosciano, et. al., have described the organoleptic properties as follows: Odor as "Sweet, creamy, waxy, lactonic, coconut, rich, milky" and taste as "Sweet, creamy, lactonic, waxy, milky, coconut and tropical" at 30 ppm.

Flavor Threshold (in water) = 150 ppb
Creamy, peachy, fatty odor; cream-like taste

delta-Dodecalactone or 5-heptylpentanolide...C12H22O2

..........................
occurs in products such as Butter, Coconut, Cream, Milk. Mosciano, et. al., have described the organoleptic properties as follows: Odor as "Sweet, creamy, waxy, lactonic, coconut, rich, milky" and taste as "Sweet, creamy, lactonic, waxy, milky, coconut and tropical" at 30 ppm.

Odor Detection Threshold (in water) = 160 ppb
Creamy, peachy, fatty odor; cream-like taste

Massoia lactone or 5-Pentylpent-2-en-5-olide...C10H16O2

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occurs in products such as Ant species, Burley Tobacco, Massoia oil, Osmanthus, Sugar Molasses, Tuberose, Wine. Mosciano et. al. (1994) describes the odor as "sweet, coconut meat, lactonic, creamy, milky and waxy" and the taste (at 20 ppm) as creamy, coconut, milky, green and slightly fruity".

Odor Detection Threshold (in water) = NA
Powerful creamy, coconut character

Jasmine lactone or Z-2-Pentenylpentan-5-olide...C10H16O2

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also known as Z-Dec-7-en-5-olide, occurs in products such as Gardenia flowers, Jasmine, Osmanthus, Tea, Tuberose. Bedoukian describes this material as "powerful, creamy, jasmine-peachy-coconut". Jasmine lactone or (-)-(R)-(Z)-Dec-7-en-5-olide is present in Jasmine absolute at 0.5-1.5% and is an important contributor to the sweet warm diffusive floral character. Its optical antipode (+)-(S)-(Z)-Dec-7-en-5-olide occurs in Tuberose.

Odor Detection Threshold (in water) = 2000 ppb
Powerful, oily-fatty, fruity, Peach-Apricot notes

6-Pentyl-alpha-pyrone or 5-Pentylpenta-2,4-dien-5-olide...C10H14O2

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also known as Deca-2,4-dien-5-olide, occurs in products such as Cooked Beef, Mushroom, Osmanthus, Peach. Mosciano, et. al. report that this material has a "coconut, creamy, sweet, brown with a fatty waxy nuance" odor and a "sweet, creamy, coconut, mushroom and nutty" taste at 30 ppm.

Odor Detection Threshold (in water) = 150 ppb
Powerful coconut, creamy-buttery odor

 Data abstracted from Flavor-Base
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