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Odor
Properties & Molecular
Visualization
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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
..........................
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
..........................
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
.........................
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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1989-2010
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