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citronellyl (R)-lactate

Citronellyl (R)-lactate is an organic ester used mainly as a fragrance ingredient with a floral lily-of-the-valley odor.
Chemical Structure

General Material Description

Citronellyl (R)-lactate is an organic ester characterized by the molecular formula C13H24O3. It is a colorless to pale liquid typically recognized for its floral odor resembling lily of the valley, combined with a warm and rich natural note. This compound is identified by its systematic name 3,7-dimethyl-6-octen-1-yl (2R)-2-hydroxypropanoate and is known by several synonyms including rosilial plus. Citronellyl (R)-lactate is primarily sourced through synthetic esterification processes involving citronellol derivatives and lactic acid. It is indexed in chemical registries such as PubChem with CID 57375717, providing comprehensive structural and physicochemical data. Due to its olfactory qualities, it is valued in fragrance synthesis and related applications.

Occurrence, Applicability & Potential Uses

Although citronellyl (R)-lactate may not be a naturally occurring metabolite, it derives structurally from compounds found in natural essential oils, notably citronellol. Its main applications lie in perfumery and fragrance formulations where it imparts a distinct floral character. The compound’s suitability for fragrance use is governed by standards including IFRA (Global), which provides guidelines on concentration limits and safe application. Citronellyl (R)-lactate is predominantly used as a fragrance agent in fine fragrances, personal care products, and household scent formulations. It should be noted that it is not intended for flavor use according to current regulatory recommendations.

Physico-Chemical Properties Summary

Citronellyl (R)-lactate presents moderate volatility and a relatively high flash point measured at 256 °F, contributing to its stability in fragrance formulations. Its estimated log P value of approximately 3.4 indicates moderate lipophilicity, favoring solubility in organic solvents such as alcohols while exhibiting limited water solubility measured near 100 mg/L at 25 °C. These properties influence its diffusion and evaporation behavior in ambient environments. The compound exists as a chiral ester, which can affect its sensory profile and interaction with olfactory receptors. Its physical state as a liquid at room temperature and appreciable stability make it compatible with various topical and air dispersion products.

FAQ

What is citronellyl (R)-lactate and what are its key characteristics?
Citronellyl (R)-lactate is an organic ester commonly used as a fragrance ingredient. It is known for its floral odor, often described as lily of the valley with warm, rich natural notes. Structurally, it consists of a citronellyl moiety esterified to (R)-lactic acid. The compound is a colorless liquid with the formula C13H24O3 and is recognized under several synonyms, including rosilial plus. It functions primarily in perfumery and related scent applications.
How is citronellyl (R)-lactate used and where is it typically applied?
Citronellyl (R)-lactate is applied predominantly as a fragrance agent in perfumes, personal care products, and household items. Its floral scent profile makes it desirable for creating delicate and natural-smelling compositions. The compound is soluble in alcohol solvents, facilitating its inclusion in various liquid and spray formulations. It is not approved for flavor use and is generally synthesized for controlled usage in fragrance manufacturing. Regulatory guidance such as the IFRA Code of Practice (Global) informs its maximum concentration levels to ensure safe application.
What are the regulatory considerations and sourcing information for citronellyl (R)-lactate?
Citronellyl (R)-lactate is subject to evaluation by fragrance regulatory bodies including IFRA (Global), which issues recommendations on safe usage levels and application restrictions. According to current data, it is not recommended for flavoring purposes but is accepted within established limits for fragrance use. The compound is synthesized chemically rather than extracted from natural sources, ensuring consistent purity and supply. Comprehensive safety assessments have found no significant hazard classifications under OSHA (US) standards. Industry resources such as the RIFM Fragrance Material Safety Assessment provide in-depth safety profiles.

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

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Other Information

General Material Information

Preferred name citronellyl (R)-lactate
Trivial Name 3,7-Dimethyl-6-octen-1-yl (2R)-2-hydroxypropanoate
Short Description 3,7-dimethyloct-6-enyl (R)-2-hydroxypropionic acid
Formula C13 H24 O3
CAS Number 211238-85-6
FDA UNII Search
xLogP3-AA 3.50 (est)
NMR Predictor External link
Synonyms
  • (3RS)- citronellyl (2R)-lactate
  • (3RS)-(2R)- citronellyl lactate
  • (3RS)-7-dimethyl oct-6-enyl (2R)-2-hydroxypropanoate
  • 3,7-dimethyloct-6-enyl (2R)-2-hydroxypropanoic acid
  • 3,7-dimethyloct-6-enyl (R)-2-hydroxypropionic acid
  • rosilial plus
  • 3,7-dimethyloct-6-enyl (2R)-2-hydroxypropanoate
  • Propanoic acid, 2-hydroxy-, 3,7-dimethyl-6-octen-1-yl ester, (2R)-
  • Propanoic acid, 2-hydroxy-, 3,7-dimethyl-6-octenyl ester, (2R)-
  • 3,7-Dimethyl-6-octen-1-yl (2R)-2-hydroxypropanoate

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 228.33187866211
Flash Point TCC Value 124.5 °C TCC
logP (o/w) 3.381 est
Solubility
alcohol Yes
water, 100.4 mg/L @ 25 °C (est) Yes
water No

Organoleptic Properties

Odor Type: Floral
floral, lily of the valley, warm, natural
General comment At 100.00 %. floral lily of the valley warm rich natural

Potential Uses

Applications
Odor purposes Floral

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:
fragrance agents
RIFM Fragrance Material Safety Assessment: Search
IFRA Code of Practice Notification of the 49th Amendment to the IFRA Code of Practice
Recommendation for citronellyl (R)-lactate flavor usage levels up to:
not for flavor use.

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 :57375717
National Institute of Allergy and Infectious Diseases:Data
3,7-dimethyloct-6-enyl (2R)-2-hydroxypropanoate