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2,6-dipropyl-5,6-dihydro-2H-thiopyran-3-carboxaldehyde

2,6-dipropyl-5,6-dihydro-2H-thiopyran-3-carboxaldehyde is a sulfur-containing aldehyde with a fruity, green odor, used predominantly as a flavoring agent in food products.

General Material Description

2,6-dipropyl-5,6-dihydro-2H-thiopyran-3-carboxaldehyde is a sulfur heterocyclic compound characterized by the molecular formula C12H20OS. It appears as a colorless or slightly yellow liquid and is recognized for its distinctive green and fruity odor profile, often described as reminiscent of green mango and cassis with savory and spicy undertones. This compound is also known by synonyms including 2,6-dipropyl-5,6-dihydro-2H-thiopyran-3-carbaldehyde and 3,6-dihydro-2,6-dipropyl-2H-thiopyran-5-carboxaldehyde. Its structural details and chemical information are cataloged under PubChem (CID 71396131). This flavoring substance is typically synthesized for use in food formulations to impart complex aroma notes and is not naturally derived from biological sources.

Occurrence, Applicability & Potential Uses

2,6-dipropyl-5,6-dihydro-2H-thiopyran-3-carboxaldehyde does not occur naturally in notable quantities but is commonly utilized as a synthetic flavoring agent. Its potent green and fruity odor characteristics enable its application in diverse food products, including nonalcoholic and alcoholic beverages, chewing gum, confectionery frostings, frozen dairy, jams, and sweet sauces. The compound’s inclusion in formulations is governed by guidelines such as those issued by FEMA (US), which classify it under GRAS (Generally Recognized As Safe) flavoring substances, with defined usage levels to ensure safety. The flavor compound enhances sensory qualities by adding fresh, tropical, and complex aromatic nuances to the finished products.

Physico-Chemical Properties Summary

This compound has a molecular weight of approximately 212.36 g/mol and a moderately hydrophobic nature indicated by an estimated XLogP value of 3.40. It demonstrates limited water solubility, measured at around 16.88 mg/L at 25 °C, suggesting preferential solubility in organic solvents suitable for flavor formulation. The physicochemical profile supports its stability and effectiveness in lipid-rich and aqueous food matrices at typical usage levels. Its sulfur atom within the thiopyran ring contributes to the characteristic odor and flavor nuances. These properties collectively influence its volatility, interaction with other flavor components, and sensory impact in complex food systems.

FAQ

What is 2,6-dipropyl-5,6-dihydro-2H-thiopyran-3-carboxaldehyde and its flavor characteristics?
2,6-dipropyl-5,6-dihydro-2H-thiopyran-3-carboxaldehyde is a synthetic sulfur-containing aldehyde noted for its distinctive green and fruity odor profile. It exhibits aroma notes reminiscent of green mango, cassis, and tropical fruits, accompanied by subtle savory and spicy undertones. This compound is used primarily as a flavoring agent to impart complex sensory nuances to food products.
How is 2,6-dipropyl-5,6-dihydro-2H-thiopyran-3-carboxaldehyde applied and what are its common uses?
This flavor compound is applied in various food categories, including nonalcoholic and alcoholic beverages, chewing gum, confectionery frostings, frozen dairy products, jams, and sweet sauces. It is employed to deliver fresh, tropical, and green aromatic characteristics. Due to moderate water solubility and lipophilic properties, it is compatible with diverse food formulations, enhancing flavor complexity without dominating the blend.
What regulatory standards govern the use of 2,6-dipropyl-5,6-dihydro-2H-thiopyran-3-carboxaldehyde and where can safety information be found?
The compound is recognized under FEMA (US) as a GRAS flavoring substance with specified recommended use levels across numerous food categories. No hazard classifications are reported under OSHA or GHS standards, and toxicological data remain limited. Comprehensive safety information and regulatory references are accessible via databases such as the FEMA Flavor Ingredient Library, FDA regulations, and PubChem. Its use excludes fragrance applications, focusing strictly on flavor.

US / EU / FDA / JECFA / FEMA / Scholar / Patents

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General Material Information

Preferred name 2,6-dipropyl-5,6-dihydro-2H-thiopyran-3-carboxaldehyde
Trivial Name 2,6-dipropyl-5,6-dihydro-2H-thiopyran-3-carbaldehyde
Short Description 2H-thiopyran-5-carboxaldehyde, 3,6-dihydro-2,6-dipropyl
Formula C12 H20 O S
CAS Number 61407-00-9
FEMA Number 4822
FDA UNII OTY1T56CSO
Nikkaji Number J3.416.553J
xLogP3-AA 3.40 (est)
NMR Predictor External link
FDA Patent No longer provide for the use of these seven synthetic flavoring substances
Synonyms
  • 3,6-dihydro-2,6-dipropyl-2H-thiopyran-5-carboxaldehyde
  • 2H- thiopyran-5-carboxaldehyde, 3,6-dihydro-2,6-dipropyl

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 212.3556060791
Solubility
water, 16.88 mg/L @ 25 °C (est) Yes

Organoleptic Properties

Odor Type: Green
green, mango, tropical
General comment At 1.00 % in propylene glycol. green mango tropical
Flavor Type: Fruity
fruity, green, currant bud black currant bud, savory, spicy
General comment Fruity, green, cassis, savory and spicy

Safety Information

Safety information

Hazards identification
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
Pictogram
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined

Safety in use information

Category:
flavoring agents
Recommendation for 2,6-dipropyl-5,6-dihydro-2H-thiopyran-3-carboxaldehyde usage levels up to:
not for fragrance use.
Use levels for FEMA GRAS flavoring substances on which the FEMA Expert Panel based its judgments that the substances are generally recognized as safe (GRAS).
The Expert Panel also publishes separate extensive reviews of scientific information on all FEMA GRAS flavoring substances and can be found at FEMA Flavor Ingredient Library
publication number: 28
Click here to view publication 28
average usual ppmaverage maximum ppm
baked goods: --
beverages(nonalcoholic): 0.050005.00000
beverages(alcoholic): 0.0300010.00000
breakfast cereal: --
cheese: --
chewing gum: 10.00000100.00000
condiments / relishes: --
confectionery froastings: 0.3000030.00000
egg products: --
fats / oils: --
fish products: --
frozen dairy: 0.5000050.00000
fruit ices: 0.050005.00000
gelatins / puddings: 0.2000010.00000
granulated sugar: --
gravies: --
hard candy: 0.5000050.00000
imitation dairy: 0.050005.00000
instant coffee / tea: 0.050005.00000
jams / jellies: 0.5000020.00000
meat products: --
milk products: 0.050005.00000
nut products: --
other grains: --
poultry: --
processed fruits: 0.050005.00000
processed vegetables: --
reconstituted vegetables: --
seasonings / flavors: 0.5000020.00000
snack foods: --
soft candy: 0.200005.00000
soups: --
sugar substitutes: --
sweet sauces: 0.2000010.00000

Safety references

EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :71396131
National Institute of Allergy and Infectious Diseases:Data
2,6-dipropyl-5,6-dihydro-2H-thiopyran-3-carbaldehyde
Chemidplus:0061407009