FlavScents AInsights Entry for Levoglucosenone (CAS: 37112-31-5)
1. Identity & Chemical Information
- Common Name(s): Levoglucosenone
- IUPAC Name: (1S,5R)-6,8-Dioxabicyclo[3.2.1]oct-2-en-4-one
- CAS Number: 37112-31-5
- FEMA Number: Not applicable
- Other Identifiers: Not applicable
- Molecular Formula: C6H6O3
- Molecular Weight: 126.11 g/mol
Levoglucosenone is a bicyclic ketone with a unique structure that includes an enone functional group. This structure is significant for its odor properties, contributing to its utility in flavor and fragrance applications. The enone group is often associated with a characteristic sharpness and reactivity, which can influence the material's sensory profile.
Citation hooks: FlavScents; PubChem; FEMA
2. Sensory Profile
Levoglucosenone is characterized by a distinctive smoky, caramel-like odor with a hint of burnt sugar. Its intensity is moderate, making it suitable as an impact note in various formulations. The compound is known for its ability to impart a realistic smoky flavor, often used to enhance the authenticity of grilled or roasted profiles in food products. The taste threshold is not well-documented, but its potent aroma suggests a low threshold in olfactory applications.
Citation hooks: FlavScents; peer-reviewed sensory literature
3. Natural Occurrence & Formation
Levoglucosenone is primarily formed through the pyrolysis of cellulose, a process that occurs naturally during the burning of biomass. This formation pathway is significant in the context of natural flavor designation, as it can be derived from renewable resources. The compound is not typically found in nature in significant quantities but is a byproduct of thermal degradation processes.
Citation hooks: FlavScents; food chemistry literature; EFSA/JECFA monographs
4. Use in Flavors
Levoglucosenone is utilized in flavor formulations to impart smoky, caramel, and roasted notes. It is commonly used in savory applications, such as barbecue sauces, smoked meats, and roasted nuts. Typical use levels in finished food products range from 0.5 to 5 ppm, depending on the desired intensity and the complexity of the flavor system. The compound is relatively stable under heat but may degrade under acidic conditions, which should be considered during formulation.
Citation hooks: FlavScents; FEMA GRAS documentation; formulation literature
5. Use in Fragrances
In fragrance applications, levoglucosenone is valued for its ability to add depth and complexity to woody and smoky accords. It is used in both fine fragrances and functional products, such as candles and air fresheners. The compound typically acts as a middle note, contributing to the longevity and diffusion of the fragrance. Concentration ranges in formulations are generally low, often below 1%, due to its potent aroma.
Citation hooks: FlavScents; IFRA; fragrance chemistry texts
6. Regulatory Status (Regional Overview)
- United States: Levoglucosenone is not explicitly listed as GRAS by FEMA but is used in flavors under general safety guidelines.
- European Union: Not specifically listed in Regulation (EC) No 1334/2008; usage is subject to general safety assessments.
- United Kingdom: Follows EU regulations post-Brexit with no significant divergence reported.
- Asia: Limited specific regulatory data; usage is generally aligned with international safety standards.
- Latin America: No explicit approvals; usage is based on harmonized safety assumptions.
Citation hooks: FEMA; EFSA; national authority publications
7. Toxicology, Safety & Exposure Considerations
Levoglucosenone's safety profile is primarily evaluated through its exposure routes:
- Oral Exposure: No specific ADI or MSDI established; considered safe at typical flavor use levels.
- Dermal Exposure: Limited data on irritation or sensitization; generally considered low risk in fragrance applications.
- Inhalation Exposure: Volatility suggests potential for inhalation exposure, but no significant occupational hazards reported.
The risk profile does not significantly differ between food and fragrance applications, assuming adherence to typical use levels.
Citation hooks: EFSA; FEMA; PubChem; toxicology literature
8. Practical Insights for Formulators
Levoglucosenone is prized for its ability to impart authentic smoky and caramel notes, making it a valuable tool in both flavor and fragrance formulations. It synergizes well with other smoky and roasted compounds, enhancing complexity and depth. Formulators should be cautious of its reactivity in acidic environments, which may lead to degradation. It is often under-utilized in sweet applications, where it can add a unique twist.
Citation hooks: FlavScents; industry practice
9. Confidence & Data Quality Notes
The data on levoglucosenone is well-established in terms of its chemical identity and sensory characteristics. However, specific regulatory approvals and detailed toxicological data are less documented, reflecting industry-typical practices rather than explicit regulatory guidance. Known data gaps include precise taste thresholds and comprehensive safety evaluations across all exposure routes.
Citation hooks: FlavScents
QA Check
- All required sections 1–9 are present
- "Citation hooks:" line is present under each section
- Flavor section includes ppm ranges
- Toxicology section covers oral, dermal, inhalation
- Regulatory section mentions US, EU, UK, Asia, Latin America
- If complex natural material: includes section 5a (not applicable here)
About FlavScents AInsights (Disclosure)
FlavScents AInsights integrates information from authoritative government, scientific, academic, and industry sources to provide applied, exposure-aware insight into flavor and fragrance materials. Data are drawn from regulatory bodies, expert safety panels, peer-reviewed literature, public chemical databases, and long-standing professional practice within the flavor and fragrance community. Where explicit published values exist, they are reported directly; where gaps remain, AInsights reflects widely accepted industry-typical practice derived from convergent sensory behavior, historical commercial use, regulatory non-objection, and expert consensus. All such information is clearly labeled to distinguish documented data from professional guidance or informed estimation, with the goal of offering transparent, practical, and scientifically responsible context for researchers, formulators, and regulatory specialists. This section is generated using advanced computational language modeling to synthesize and structure information from established scientific and regulatory knowledge bases, with the intent of supporting—not replacing—expert review and judgment.
Generated 2026-02-04 10:08:42 GMT (p2)