Important Synthetic Flavor Compounds - Part 7 (alpha-damascene, beta-demascone, damascenone, nootkatone, neryl acetate, geranyl acetate, citronellyl acetate, linalyl acetate, isobornyl acetate, 4-mentha-8-thiol-3-one)
Part 7 (alpha-damascene, beta-demascone, damascenone, nootkatone, neryl acetate, geranyl acetate, citronellyl acetate, linalyl acetate, isobornyl acetate, 4-mentha-8-thiol-3-one)
These are part of the 128 synthetic flavor compounds John Wright recommends in his book Flavor Creation that every flavorist should know and worth with
alpha-Damascene (alpha-Damascone)
- FEMA Number: 3659 .
- Flavor Note(s): Sweet, fruity, floral, woody with a green berry nuance. The taste is sweet, fruity, and woody with a green, seedy background .
- Compounds That Render Similar Flavor Note: beta-Damascone (more fruity, plum-like), damascenone (more intense, floral-fruity with baked fruit character), and other rose ketones.
- Compounds Often Used Together With: Used with beta-damascone, damascenone, and ionones in berry (especially raspberry and blackberry), apple, and floral flavor complexes to add depth and naturalness.
- All Potential Applications: Berry flavors (raspberry, strawberry, blackberry), apple, red fruit blends, and floral nuances for beverages, confectionery, and baked goods.
- General Usage Levels: Extremely potent. Used at very low levels, typically in the range of 0.1 to 5 ppm in the finished product.
- Important Considerations for Flavorists: Store in a cool, dry place in tightly sealed containers, protected from heat and light. It has a flash point >200°F TCC. Proper storage yields a shelf life of 12 months or longer . FEMA GRAS.
beta-Damascone
- FEMA Number: 3243 .
- Flavor Note(s): Fruity, floral, black currant, plum, rose, honey, tobacco. It has a rich, sweet, and complex fruity-floral character .
- Compounds That Render Similar Flavor Note: alpha-Damascone (more woody-green), damascenone (more intense, baked fruit), beta-ionone (woody-berry, less fruity).
- Compounds Often Used Together With: Used with damascenone, ionones, and other rose ketones in black currant, plum, rose, and honey flavor complexes. Also used in tobacco flavors.
- All Potential Applications: Black currant, plum, prune, raisin, rose, honey, and other fruit and floral flavors for beverages, candies, baked goods, and tobacco products.
- General Usage Levels: Very potent. Used at very low levels, typically from 0.1 to 5 ppm in the finished product.
- Important Considerations for Flavorists: Store in a cool, dry place in tightly sealed containers, protected from heat and light. It has a flash point >200°F TCC. Proper storage yields a shelf life of 12 months or longer . FEMA GRAS.
Damascenone
- FEMA Number: 3420 .
- Flavor Note(s): Extremely powerful, intensely natural, floral (rose), fruity (plum, grape, raspberry), and sugary. It smells intensely natural with a complex, baked fruit character .
- Compounds That Render Similar Flavor Note: beta-Damascone (plum-rose), alpha-damascone (green-berry), and the ionones (violet-berry).
- Compounds Often Used Together With: Used with other rose ketones (damascones, ionones) and fruity esters in complex fruit (berry, plum) and floral (rose) flavor compositions.
- All Potential Applications: Rose, raspberry, strawberry, plum, grape, and other fruit and floral flavors for beverages, confectionery, baked goods, and dairy products.
- General Usage Levels: Extremely potent. The maximum skin level in fine fragrances has been reported at 0.02% ; in flavors, finished product levels are typically in the low ppb to very low ppm range.
- Important Considerations for Flavorists: Acute oral LD50 in rats was >2.0 g/kg with no observed deaths, indicating low acute toxicity . It is a fragrance ingredient used in many consumer products with worldwide usage in the region of 1–10 metric tonnes per annum . JECFA (No. 387) concluded the substance does not present a safety concern at current levels of intake . Flash point >200°F CC. FEMA GRAS.
Nootkatone
- FEMA Number: 3166 .
- Flavor Note(s): Grapefruit, citrus, peely, juicy. It is the primary character-impact compound of grapefruit, providing the distinct, juicy, and slightly bitter grapefruit aroma.
- Compounds That Render Similar Flavor Note: Grapefruit oil, valencene (orange, less grapefruit-specific), other sesquiterpene ketones.
- Compounds Often Used Together With: Used with other citrus terpenes (d-limonene, valencene) and aldehydes (decanal, octanal) to build authentic grapefruit and other citrus profiles.
- All Potential Applications: Grapefruit, orange, and other citrus flavors for beverages, candies, and functional products. It is also known for its insect-repellent properties.
- General Usage Levels: Used at low to moderate levels. In finished products, typical usage ranges from 5 to 50 ppm, depending on the desired grapefruit intensity.
- Important Considerations for Flavorists: In China, it is regulated as a synthetic food flavor and can only be used for that functional purpose, with specific applicable food categories and maximum content limits as per NHC regulations . Store in a cool, dry place. FEMA GRAS.
Neryl Acetate
- FEMA Number: 2773 .
- Flavor Note(s): Sweet, floral, rose-like, raspberry. The taste is fresh, pungent, with honey notes .
- Compounds That Render Similar Flavor Note: Geranyl acetate (sweeter, more fruity-floral, lavender undertone) , citronellyl acetate (dusty, floral, rose) , linalyl acetate (citrus, bergamot, floral).
- Compounds Often Used Together With: Used with geranyl acetate, citronellyl acetate, and other terpene esters in floral (rose, neroli, jasmine) and berry (raspberry) flavor complexes.
- All Potential Applications: Rose, neroli, jasmine, raspberry, and other fruit and floral flavors for beverages, candies, and baked goods.
- General Usage Levels: Used at low to moderate levels. In finished products, typical usage ranges from 2 to 30 ppm.
- Important Considerations for Flavorists: Keep in tightly closed container in a cool and dry place, protected from light. When stored for more than 24 months, quality should be checked before use. Flash point 101°C. Soluble in ethanol 70% . FEMA GRAS.
Geranyl Acetate
- FEMA Number: 2509 .
- Flavor Note(s): Sweet, fruity-floral, rosy, green odor with a lavender undertone .
- Compounds That Render Similar Flavor Note: Neryl acetate (fresher, more honey-like), linalyl acetate (more citrus-bergamot), citronellyl acetate (softer rose).
- Compounds Often Used Together With: Used with neryl acetate, citronellyl acetate, linalool, and other terpenes in floral (rose, lavender, geranium) and fruit (apple, apricot, berry) flavor compositions.
- All Potential Applications: Rose, lavender, geranium, apple, apricot, berry, and citrus flavors for beverages, candies, baked goods, and chewing gum.
- General Usage Levels: In flavors, typical usage is up to 20 ppm in the finished product .
- Important Considerations for Flavorists: Almost colourless to pale yellow liquid. Soluble in 1.5 volumes of 70% alcohol. Flash point (TCC) >100°C. Typical shelf life is 2 years . FEMA GRAS.
Citronellyl Acetate
- FEMA Number: 2311 .
- Flavor Note(s): Dusty, floral, fragrant, rose . It provides a sweet, fresh, and fruity-rose character with a hint of citrus.
- Compounds That Render Similar Flavor Note: Geranyl acetate (more intense, lavender undertone), neryl acetate (fresher, honey-like), linalyl acetate (more citrusy).
- Compounds Often Used Together With: Used with geranyl acetate, neryl acetate, citronellol, and other rose alcohols in rose, citrus, and berry flavor complexes.
- All Potential Applications: Rose, citrus (especially bergamot), berry, and other fruit and floral flavors for beverages, candies, and baked goods.
- General Usage Levels: Used at low to moderate levels. In finished products, typical usage ranges from 2 to 30 ppm.
- Important Considerations for Flavorists: JECFA number 57 . Listed in 21CFR172.515 . Store in a cool, dry place in tightly sealed containers. FEMA GRAS.
Linalyl Acetate
- FEMA Number: 2636
- Flavor Note(s): Sweet, floral, fruity, citrus (bergamot), lavender. It has a fresh, light, and pleasant bergamot-like character with woody and spicy undertones.
- Compounds That Render Similar Flavor Note: Lavender oil, bergamot oil, geranyl acetate (rosy-lavender), linalool (the alcohol version, less fruity, more floral).
- Compounds Often Used Together With: Used with linalool, geranyl acetate, and other terpenes in lavender, bergamot, and other citrus flavors. Also used in peach, apricot, and berry complexes.
- All Potential Applications: Lavender, bergamot, orange, peach, apricot, blackberry, and other fruit and floral flavors for beverages, candies, baked goods, and chewing gum.
- General Usage Levels: Used at low to moderate levels. In finished products, typical usage ranges from 5 to 50 ppm.
- Important Considerations for Flavorists: Found naturally in many essential oils including lavender, bergamot, and clary sage. It is prone to hydrolysis in acidic environments. Store in a cool, dry place in tightly sealed containers. FEMA GRAS.
Isobornyl Acetate
- FEMA Number: 2160 .
- Flavor Note(s): Green, piney, woody, herbal, camphoraceous. It provides a fresh, clean, and characteristic pine forest aroma with a slight balsamic undertone.
- Compounds That Render Similar Flavor Note: Bornyl acetate (similar piney character), pine needle oil, fir needle oil, and other pine terpenes.
- Compounds Often Used Together With: Used with other pine terpenes (alpha-pinene, beta-pinene, camphene) and herbal notes in pine, forest fruit, and spice flavor complexes.
- All Potential Applications: Pine, fir, and other forest fruit flavors. Used in confectionery (cough drops, candies), beverages, baked goods, and some spice blends.
- General Usage Levels: Used at moderate levels. In finished products, typical usage ranges from 5 to 50 ppm.
- Important Considerations for Flavorists: JECFA number 1388 . The FEMA GRAS assessment of alicyclic substances used as flavor ingredients, including isobornyl acetate, was published in Food and Chemical Toxicology (1996) . Listed in 21CFR172.515. Store in a cool, dry place in tightly sealed containers. FEMA GRAS.
4-Mentha-8-thiol-3-one
- FEMA Number: 3809 .
- Flavor Note(s): Sulfury, catty, black currant, grapefruit, tropical. It has an intense, "tomcat" or "buchu" note that is characteristic of black currant and certain tropical fruits .
- Compounds That Render Similar Flavor Note: 4-Mentha-8-thiol-3-one acetate (softer, more stable, similar catty-berry profile) , buchu oil, other sulfur-containing compounds with catty notes.
- Compounds Often Used Together With: Used extensively in black currant flavors. Also used in grapefruit, passionfruit, guava, mango, peach, and other tropical and berry fruit flavors to add authentic sulfury lift and complexity .
- All Potential Applications: Black currant, grapefruit, passionfruit, guava, mango, peach, nectarine, lychee, cantaloupe, tangerine, and many other fruit flavors for beverages, candies, and functional products .
- General Usage Levels: Extremely potent. Dose rates in flavor concentrates vary widely by application: e.g., 1 ppm in lychee, 5 ppm in mango/lemon, 8 ppm in cantaloupe, 10-20 ppm in grapefruit/guava/peach, 20-100 ppm in passionfruit/black currant . In finished products, levels are in the low ppb range.
- Important Considerations for Flavorists: It is chemically more stable and more heat stable than the corresponding thiol, making it preferable for applications involving heat processing or requiring longer shelf life . Its catty note is relatively free from metallic undertones compared to some other sulfur compounds . Store in a cool, dark place in tightly sealed containers under inert gas to prevent oxidation. FEMA GRAS.
###