3,7-Dimethyl-1,6-nonadien-3-ol
[CAS# 10339-55-6]

Identification

• Classification: Flavors and spices >> Synthetic spice >> Alcoholic spice >> Terpene alcohol
• Name: 3,7-Dimethyl-1,6-nonadien-3-ol
• Synonyms: Ethyl linalool
• Molecular Formula: C₁₁H₂₀O
• Molecular Weight: 168.28
• CAS Registry Number: 10339-55-6
• EC Number: 233-732-6
• SMILES: CC/C(=C/CCC(C)(C=C)O)/C

Properties

• Solubility: Very slightly soluble (0.3 g/L) (25 ºC), Calc.^*
• Density: 0.857±0.06 g/cm³ (20 ºC 760 Torr), Calc.^*
• Boiling point: 132 ºC (86 Torr)^**
• Refractive index: 1.4603 (589.3 nm 25 ºC)^**
• Flash point: 90.9±15.0 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2013 ACD/Labs)

^** Surmatis, Joseph D.; US 2806882 1957.

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H317-H319
• Precautionary Statements: P261-P264-P264+P265-P272-P280-P302+P352-P305+P351+P338-P321-P332+P317-P333+P317-P337+P317-P362+P364-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Skin sensitization	Skin Sens.	1B	H317
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Skin sensitization	Skin Sens.	1	H317

Discovory and Applicatios

3,7-Dimethyl-1,6-nonadien-3-ol is an organic compound with the molecular formula C11H20O. It is a terpene alcohol commonly referred to as dihydromyrcenol. Structurally, the compound consists of a linear chain with two double bonds at positions 1 and 6, and a hydroxyl group (-OH) attached to the third carbon. Its molecular structure gives it a fresh, citrus-like scent, which has led to its extensive use in the fragrance and flavoring industries.

The discovery of 3,7-dimethyl-1,6-nonadien-3-ol is tied to the exploration of natural terpenes and their derivatives. Terpenes, a large class of naturally occurring organic compounds, are found in many plants and contribute to their aromatic properties. Myrcene, from which dihydromyrcenol is derived, is one of the most abundant monoterpenes found in essential oils such as bay, thyme, and hops. Over time, synthetic methods were developed to modify these natural terpenes, leading to the production of compounds like dihydromyrcenol, which retains the freshness of its parent structure while being more stable and easier to produce on an industrial scale.

The primary application of 3,7-dimethyl-1,6-nonadien-3-ol is in the fragrance industry. It is commonly used as a key ingredient in perfumes, soaps, and household cleaning products. Its fresh, citrusy scent with slight floral and woody notes makes it highly desirable for use in a wide range of products, particularly in formulations that aim to evoke cleanliness, freshness, and vitality. Dihydromyrcenol is especially popular in men’s fragrances due to its crisp and refreshing aroma. It is often used as a middle or top note in fragrance compositions, providing a long-lasting, clean scent profile.

Beyond its use in perfumes and personal care products, 3,7-dimethyl-1,6-nonadien-3-ol is also utilized in the flavoring industry. Although it is used in small amounts, its citrus and slightly floral characteristics make it a valuable additive in food and beverage products. It can be found in some fruit-flavored beverages, confections, and even certain baked goods where a fresh and light aroma is desired. The compound’s volatility and stability make it suitable for these applications, ensuring that its scent or flavor remains intact during processing and storage.

Another significant application of 3,7-dimethyl-1,6-nonadien-3-ol is in household and cleaning products. Its fresh scent is ideal for detergents, air fresheners, and fabric softeners, contributing to the overall sensory experience of cleanliness. In these products, the compound not only enhances the fragrance but also provides a long-lasting, pleasant odor that masks undesirable smells.

In addition to its role in fragrances and flavors, 3,7-dimethyl-1,6-nonadien-3-ol is used in industrial applications as a chemical intermediate. Its reactivity, particularly the presence of a hydroxyl group, allows it to participate in various chemical reactions. It can be used as a building block in the synthesis of more complex molecules, including other fragrance compounds or specialized chemicals for industrial use.

The production of 3,7-dimethyl-1,6-nonadien-3-ol is primarily synthetic, even though it is derived from naturally occurring terpenes like myrcene. Industrial synthesis of this compound typically involves the hydrogenation of myrcene followed by selective oxidation to introduce the hydroxyl group. This process yields a highly pure product, which is important for ensuring consistency in its fragrance and flavor applications.

While 3,7-dimethyl-1,6-nonadien-3-ol is generally considered safe for use in consumer products, it must still be handled with care, especially in concentrated forms. Like many fragrance chemicals, it can cause skin or eye irritation upon direct contact, and inhalation of concentrated vapors should be avoided. Regulatory agencies such as the International Fragrance Association (IFRA) provide guidelines on the safe usage levels of this compound in products to minimize any potential risks to consumers.

In conclusion, 3,7-dimethyl-1,6-nonadien-3-ol is a highly valuable compound in the fragrance and flavor industries due to its fresh, citrusy aroma and versatility. Its use extends from perfumes to household products and food flavoring, making it a widely utilized ingredient in everyday consumer goods. Through synthetic production methods, it is readily available for industrial use, ensuring a stable supply for various applications. As research continues into terpenes and their derivatives, 3,7-dimethyl-1,6-nonadien-3-ol is likely to maintain its importance in both consumer products and industrial chemistry.

References

2022. Update to RIFM fragrance ingredient safety assessment, 3,7-dimethyl-1,6-nonadien-3-ol, CAS Registry Number 10339-55-6. Food and Chemical Toxicology, 167.
DOI: 10.1016/j.fct.2022.113265

2016. RIFM fragrance ingredient safety assessment, 3,7-dimethyl-1,6-nonadien-3-ol, CAS Registry Number 10339-55-6. Food and Chemical Toxicology, 97.
DOI: 10.1016/j.fct.2016.09.024

2010. Fragrance material review on 3,7-dimethyl-1,6-nonadien-3-ol. Food and Chemical Toxicology, 48.
DOI: 10.1016/j.fct.2009.11.010