Important Synthetic Flavor Compounds - Part 5 (cis-3-hexenyl acetate, cis-3-hexenyl butyrate, methyl mercaptan, dimethyl sulfide, methional,methyl thiobutyrate, methyl 3-methylthiopropionate, cyclotene, methyl jasmonate, linalool)

These are among the 128 synthetic flavor compounds that John Wright, in his book Flavor Creation, suggests every flavorist should know and work with.

Part 5 (cis-3-hexenyl acetate, cis-3-hexenyl butyrate, methane thiol or methyl mercaptan, dimethyl sulfide, 3-(methylthio) propanal,methyl thiobutyrate, methyl 3-methylthiopropionate, 3-methylcyclopentane-1,2-dione, methyl jasmonate,
linalool)

Here are the 10 compounds in the enhanced format consistent with the previous series:

cis-3-Hexenyl Acetate

• CAS Number: 3681-71-8
• FEMA Number: 3171
• Regulatory Status: FEMA GRAS. JECFA No. 135.
• Flavor Note(s): Powerful, green, fruity, banana, pear, apple, with a characteristic fresh, leafy undertone. The acetate ester of cis-3-hexenol provides a sweeter, more fruity character compared to the alcohol.
• Odor Threshold: Approximately 1–10 ppb in water
• Compounds That Render Similar Flavor Note: cis-3-Hexenol (greener, more grassy), cis-3-hexenyl butyrate (softer, more buttery-fruity), hexyl acetate (less green, more fruity).
• Compounds Often Used Together With: Used extensively with cis-3-hexenol, cis-3-hexenyl butyrate, and other green esters in apple, pear, banana, and strawberry flavors. Also used in tea, jasmine, and other floral-green complexes.
• All Potential Applications: Apple, pear, banana, strawberry, melon, and tropical fruit flavors. Also used in green tea, jasmine, and vegetable profiles to add fresh, green top notes.
• General Usage Levels: In finished products: 0.5–15 ppm. In flavor concentrates: 0.005–0.15% (50–1500 ppm). For apple/pear: 2–10 ppm; for banana: 3–12 ppm; for strawberry: 1–8 ppm.
• Safety & Handling: Colorless to pale yellow liquid. Flash point: 140°F (60°C). Store in a cool, dry place in tightly sealed containers, protected from light. Stable under normal storage conditions. Shelf life: 24 months.

cis-3-Hexenyl Butyrate

• CAS Number: 16491-36-4
• FEMA Number: 3402
• Regulatory Status: FEMA GRAS
• Flavor Note(s): Green, fruity, fresh, with a sweet, buttery, and slightly tropical nuance. Softer and more rounded than cis-3-hexenyl acetate, with a pleasant pear-apple character.
• Odor Threshold: Approximately 1–10 ppb in water
• Compounds That Render Similar Flavor Note: cis-3-Hexenyl acetate (sharper, more banana-like), cis-3-hexenol (greener, less fruity), hexyl butyrate (less green, more fruity).
• Compounds Often Used Together With: Used with cis-3-hexenol, cis-3-hexenyl acetate, and other green and fruity esters in apple, pear, strawberry, and tropical fruit flavors. Adds a smooth, buttery-green depth to fruit complexes.
• All Potential Applications: Apple, pear, strawberry, banana, tropical fruits, and berry flavors. Also used in some floral and tea profiles for added naturalness.
• General Usage Levels: In finished products: 0.5–15 ppm. In flavor concentrates: 0.005–0.15% (50–1500 ppm). For apple/pear: 2–10 ppm; for strawberry: 1–8 ppm; for tropical: 2–12 ppm.
• Safety & Handling: Colorless to pale yellow liquid. Flash point: >200°F (>93°C). Store in a cool, dry place in tightly sealed containers, protected from light. Stable under normal storage conditions. Shelf life: 24 months.

Methane Thiol (Methyl Mercaptan)

• CAS Number: 74-93-1
• FEMA Number: 2716
• Regulatory Status: FEMA GRAS. Subject to strict usage limits due to extreme potency and toxicity at high concentrations.
• Flavor Note(s): Extremely powerful, pungent, garlic, cabbage, putrid, sulfurous, with a characteristic "rotten egg" or "natural gas" odor at high concentrations. At extremely low dilutions, contributes to cheese, coffee, and savory notes.
• Odor Threshold: Extremely low; approximately 0.02–0.2 ppb in water (0.00002–0.0002 ppm)
• Compounds That Render Similar Flavor Note: Dimethyl sulfide (cabbage, corn, less pungent), dimethyl disulfide (onion, cabbage, more roasted), ethyl mercaptan (similar pungency, more garlic-onion).
• Compounds Often Used Together With: Used sparingly with other sulfur compounds (dimethyl sulfide, dimethyl disulfide, thiazoles) in cheese, coffee, meat, and savory flavors to add authenticity and depth.
• All Potential Applications: Cheese flavors (especially Cheddar, Swiss), coffee, meat (beef, chicken), savory snacks, and some vegetable profiles where a sulfurous, cooked note is desired.
• General Usage Levels: Extremely potent. In finished products: 0.001–0.1 ppb (0.000001–0.0001 ppm). In flavor concentrates: 0.000001–0.0001% (0.01–1 ppm). Always handle as an extremely diluted solution (0.001–0.01% in solvent).
• Safety & Handling: Colorless gas or volatile liquid. Boiling point: 42°F (6°C). Extremely flammable. Flash point: -54°F (-48°C). Toxic by inhalation. Lachrymator. Must be handled under fume hood with extreme care using appropriate PPE. Store as a dilute solution in tightly sealed containers under inert gas. Due to extreme odor and toxicity, use only in well-ventilated areas with strict safety protocols. Shelf life: 12 months when stored properly as dilute solution.

Dimethyl Sulfide

• CAS Number: 75-18-3
• FEMA Number: 2746
• Regulatory Status: FEMA GRAS. JECFA No. 452.
• Flavor Note(s): Powerful, sulfurous, cabbage, corn, asparagus, seafood, tomato. At low dilutions, contributes a sweet, cooked vegetable, and marine character.
• Odor Threshold: Extremely low; approximately 0.3–3 ppb in water
• Compounds That Render Similar Flavor Note: Dimethyl disulfide (more cooked, onion-garlic), dimethyl trisulfide (more intense, cooked vegetable), methional (potato, cooked).
• Compounds Often Used Together With: Used with other sulfur compounds, pyrazines, and aldehydes in tomato, corn, asparagus, seafood, and savory flavors. Key component in cooked vegetable and marine profiles.
• All Potential Applications: Tomato, corn, asparagus, cooked vegetable flavors, seafood (crab, shrimp, clam), cheese, coffee, and tropical fruit nuances.
• General Usage Levels: Very potent. In finished products: 0.01–2 ppm. In flavor concentrates: 0.0001–0.02% (1–200 ppm). For tomato: 0.05–0.5 ppm; for corn: 0.1–1 ppm; for seafood: 0.2–2 ppm.
• Safety & Handling: Colorless to pale yellow liquid. Extremely flammable. Flash point: -36°F (-38°C). Volatile. Store in tightly sealed containers away from ignition sources under inert gas. Use adequate ventilation. Shelf life: 12–24 months.

3-(Methylthio) Propanal (Methional)

• CAS Number: 3268-49-3
• FEMA Number: 2747
• Regulatory Status: FEMA GRAS
• Flavor Note(s): Powerful, sulfurous, cooked potato, vegetable broth, meaty, savory. Characteristic of boiled potatoes and savory broths.
• Odor Threshold: Extremely low; approximately 0.2–1 ppb in water
• Compounds That Render Similar Flavor Note: Methionine (the amino acid precursor), 3-(methylthio) propanol (alcohol version, less intense), dimethyl sulfide (cabbage, less meaty).
• Compounds Often Used Together With: Used with pyrazines, thiazoles, and other sulfur compounds in potato, meat, savory, and cheese flavors. Key component in chicken, beef, and vegetable broth profiles.
• All Potential Applications: Potato flavors (mashed, boiled, french fry), meat flavors (chicken, beef), vegetable broths, cheese, and savory snacks.
• General Usage Levels: Very potent. In finished products: 0.05–3 ppm. In flavor concentrates: 0.0005–0.03% (5–300 ppm). For potato: 0.5–2 ppm; for meat/broth: 0.2–1.5 ppm; for cheese: 0.1–1 ppm.
• Safety & Handling: Colorless to pale yellow liquid. As an aldehyde, prone to oxidation and polymerization. Store under inert gas (nitrogen) in a cool, dark place in tightly sealed containers. Use adequate ventilation. Shelf life: 12–18 months when properly stored.

Methyl Thiobutyrate

• CAS Number: 2432-51-1
• FEMA Number: 3310
• Regulatory Status: FEMA GRAS
• Flavor Note(s): Sulfurous, fruity, pineapple, tropical, cheese, with a sharp, pungent edge. Combines fruity ester character with sulfurous intensity.
• Odor Threshold: Very low; approximately 0.5–5 ppb in water
• Compounds That Render Similar Flavor Note: Methyl 3-methylthiopropionate (tropical, pineapple, less cheesy), ethyl thiobutyrate (similar, more ethereal), methyl thioacetate (sharper, more pungent).
• Compounds Often Used Together With: Used with other sulfurous esters and tropical fruit notes in pineapple, mango, passionfruit, and cheese flavors. Adds complexity and depth to fruit and savory profiles.
• All Potential Applications: Pineapple, mango, tropical fruit flavors, cheese flavors (especially aged), and some meaty and savory applications.
• General Usage Levels: Very potent. In finished products: 0.05–5 ppm. In flavor concentrates: 0.0005–0.05% (5–500 ppm). For tropical fruit: 0.5–3 ppm; for cheese: 0.2–2 ppm.
• Safety & Handling: Colorless to pale yellow liquid. Flammable. Store in a cool, dry place in tightly sealed containers, protected from light. Sulfur compound; may cause olfactory fatigue. Use adequate ventilation. Shelf life: 12–24 months.

Methyl 3-Methylthiopropionate

• CAS Number: 13532-18-8
• FEMA Number: 2720
• Regulatory Status: FEMA GRAS
• Flavor Note(s): Sulfurous, tropical, pineapple, passionfruit, tomato, with a sweet, fruity, and slightly cooked vegetable nuance.
• Odor Threshold: Very low; approximately 0.1–1 ppb in water
• Compounds That Render Similar Flavor Note: Methyl thiobutyrate (more cheesy, less tropical), ethyl 3-methylthiopropionate (softer, more fruity), methional (more potato, less fruity).
• Compounds Often Used Together With: Used with other sulfurous compounds and fruity esters in pineapple, passionfruit, mango, and tomato flavors. Key component in tropical fruit and savory-fruit blends.
• All Potential Applications: Pineapple, passionfruit, mango, tropical fruit blends, tomato, and some cheese and savory applications.
• General Usage Levels: Very potent. In finished products: 0.05–5 ppm. In flavor concentrates: 0.0005–0.05% (5–500 ppm). For tropical fruit: 0.5–4 ppm; for tomato: 0.2–2 ppm.
• Safety & Handling: Colorless to pale yellow liquid. Store in a cool, dry place in tightly sealed containers, protected from light. As a sulfur compound, may cause olfactory fatigue. Use adequate ventilation. Shelf life: 12–24 months.

3-Methylcyclopentane-1,2-dione (Cyclotene)

• CAS Number: 80-71-7
• FEMA Number: 3435
• Regulatory Status: FEMA GRAS
• Flavor Note(s): Sweet, caramel, maple, nutty, coffee, with a warm, burnt sugar character. Used extensively as a caramel and maple flavor enhancer.
• Odor Threshold: Approximately 10–100 ppb in water
• Compounds That Render Similar Flavor Note: Maltol (softer, more cotton candy-like), ethyl maltol (more intense, sweeter), furaneol (strawberry-caramel), 2,3-pentanedione (buttery-caramel).
• Compounds Often Used Together With: Used with maltol, ethyl maltol, vanillin, and furaneol in caramel, maple, butterscotch, coffee, and nut flavors. Enhances sweetness and provides warm, brown notes.
• All Potential Applications: Caramel, maple syrup, butterscotch, coffee, nut (hazelnut, pecan), tobacco, and baked good flavors.
• General Usage Levels: In finished products: 5–100 ppm. In flavor concentrates: 0.05–1.0% (500–10,000 ppm). For caramel/maple: 10–60 ppm; for coffee: 5–30 ppm; for nut: 5–25 ppm.
• Safety & Handling: White to pale yellow crystalline solid. Melting point: 105–108°F (41–42°C). Flash point: >200°F (>93°C). Store in a cool, dry place in tightly sealed containers, protected from light and moisture. Shelf life: 24 months.

Methyl Jasmonate

• CAS Number: 1211-29-6 (cis-isomer, primary form) / 39924-52-2 (mixture)
• FEMA Number: 3411
• Regulatory Status: FEMA GRAS
• Flavor Note(s): Sweet, floral, jasmine, green, fruity, with a complex tea-like and woody undertone. Natural constituent of jasmine oil and tea.
• Odor Threshold: Approximately 0.5–5 ppb in water
• Compounds That Render Similar Flavor Note: Jasmonic acid (more acidic, less floral), methyl dihydrojasmonate (softer, more floral), cis-jasmone (more jasmine, less green).
• Compounds Often Used Together With: Used with cis-jasmone, linalool, benzyl acetate, and other floral notes in jasmine, tea, and floral flavors. Also used in apple, strawberry, and tropical fruit complexes for added depth and naturalness.
• All Potential Applications: Jasmine, tea (green tea, oolong), floral flavors, apple, strawberry, tropical fruit, and some wine and tobacco profiles.
• General Usage Levels: Used at low levels. In finished products: 0.1–10 ppm. In flavor concentrates: 0.001–0.1% (10–1000 ppm). For jasmine/floral: 0.5–8 ppm; for tea: 0.2–5 ppm; for apple/strawberry: 0.1–3 ppm.
• Safety & Handling: Colorless to pale yellow viscous liquid. Store in a cool, dry place in tightly sealed containers, protected from light. Stable under normal storage conditions. Shelf life: 24 months.

Linalool

• CAS Number: 78-70-6
• FEMA Number: 2635
• Regulatory Status: FEMA GRAS. One of the most widely used flavor and fragrance compounds globally.
• Flavor Note(s): Sweet, floral, citrus, bergamot, lavender, woody, with a fresh, light, and uplifting character. Occurs naturally in over 200 essential oils.
• Odor Threshold: Approximately 1–10 ppb in water
• Compounds That Render Similar Flavor Note: Linalyl acetate (more fruity, less floral), geraniol (more rose-like), citronellol (softer rose), terpineol (more lilac-pine).
• Compounds Often Used Together With: Used extensively with linalyl acetate, geraniol, citronellol, and other terpenes in lavender, bergamot, citrus, and floral flavors. Key component in many fruit, spice, and tea profiles.
• All Potential Applications: Lavender, bergamot, orange, lemon, grapefruit, peach, apricot, berry, tea, spice, and floral flavors for beverages, confectionery, baked goods, and chewing gum.
• General Usage Levels: Used at low to moderate levels. In finished products: 2–50 ppm. In flavor concentrates: 0.02–0.5% (200–5000 ppm). For lavender/bergamot: 10–40 ppm; for citrus: 5–25 ppm; for fruit/floral: 3–20 ppm; for tea: 2–15 ppm.
• Safety & Handling: Colorless to pale yellow liquid. Flash point: 174°F (79°C). May cause skin sensitization in susceptible individuals. Store in a cool, dry place in tightly sealed containers, protected from light. Stable under normal storage conditions. Shelf life: 24 months.

Summary Table

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