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marine nitrile

Marine nitrile is a fragrance compound known for its medium-strength citrus and marine odor notes, used primarily as a perfuming agent.
Chemical Structure

General Material Description

Marine nitrile, also referred to as cyclomugual nitrile (PFW) or by its systematic name 1,2,3,4,5,6,7,8-octahydro-8,8-dimethyl-2-naphthalenecarbonitrile, is a synthetic organic compound used in fragrance formulations. It presents as a colorless to pale liquid with a molecular formula of C13H19N and a molecular weight of approximately 189.3 g/mol. The compound offers a distinctive olfactory profile described as citrus, marine, and earthy, making it valuable as a perfuming agent. This nitrile derivative features characteristics documented in the PubChem database (CID 166374). Marine nitrile is typically synthesized for industrial use rather than sourced from natural materials, and it is incorporated into fragrances to impart fresh, aquatic, and citrus nuances.

Occurrence, Applicability & Potential Uses

Marine nitrile does not naturally occur in the environment but is manufactured for specific applications in the fragrance industry. Its odor qualities include citrus and marine notes with an earthy undertone, which make it suitable for enhancing leather, powder, spice, tobacco, and woody fragrance compositions. The compound's performance and safety parameters align with regulatory frameworks such as the IFRA Code of Practice (Global), which provides usage level recommendations for fragrance ingredients. Being primarily used as a perfuming agent, marine nitrile's application focuses on imparting complex sensory profiles in perfumes and related scented products.

Physico-Chemical Properties Summary

Marine nitrile exhibits physical and chemical properties that influence its formulation and handling. It is a stable compound with an estimated log P of 3.895, indicating moderate lipophilicity. At atmospheric pressure, its boiling point ranges between 305 and 307°C, suggesting low volatility under ambient conditions. Vapor pressure at 25°C is very low (approximately 0.001 mmHg), which correlates with its low evaporation rate. The flash point is around 93°C (200°F), so precautions should be observed for flammability at elevated temperatures. Solubility data indicates it dissolves in alcohol and very slightly in water (estimated 4.681 mg/L at 25°C). The molecule’s structure presents resilience against alkalis, reflecting chemical stability, which is beneficial for storage and formulation longevity.

FAQ

What is marine nitrile and what are its key characteristics?
Marine nitrile is a synthetic fragrance compound classified chemically as 1,2,3,4,5,6,7,8-octahydro-8,8-dimethyl-2-naphthalenecarbonitrile. It offers a medium-strength odor with notable citrus and marine notes combined with earthy undertones. The compound is widely used in perfumery due to these unique olfactory properties and presents as a stable, moderately lipophilic liquid with a molecular weight of 189.3 g/mol.
How is marine nitrile used and where is it typically applied?
Marine nitrile is employed mainly as a perfuming agent in fragrance formulations. Its scent profile makes it suitable for use in compositions evoking leather, powder, spice, tobacco, and woody themes. Due to its moderate substantivity of about 16 hours at full concentration, it contributes lasting notes in perfumes and related scented consumer products. It is a manufactured substance without natural biological occurrence, optimized for industrial fragrance applications.
What are the regulatory considerations and safety guidelines for marine nitrile?
Safety assessments for marine nitrile indicate no classified hazards under the Globally Harmonized System (GHS) according to OSHA regulations in the US. The International Fragrance Association (IFRA Global) provides guidelines recommending usage levels up to 0.8% in fragrance concentrates. It is not approved for flavor use. Safety data and regulatory references are accessible through authoritative databases such as the European Chemicals Agency (ECHA) and RIFM Fragrance Material Safety Assessments. Manufacturers and formulators follow these standards to ensure compliant and safe utilization.

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Other Information

(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
HMDB (The Human Metabolome Database):Search
Export Tariff Code:2926.90.0000
ChemSpider:View

General Material Information

Preferred name marine nitrile
Trivial Name 1,2,3,4,5,6,7,8-Octahydro-8,8-dimethyl-2-naphthalenecarbonitrile
Short Description cyclomugual nitrile (PFW)
Formula C13 H19 N
CAS Number 72928-51-9
ECHA Number 277-081-6
FDA UNII EB12VHM8TR
Nikkaji Number J296.415E
xLogP3-AA 2.80 (est)
NMR Predictor External link
Synonyms
  • cyclomugual nitrile (PFW)
  • 8,8-dimethyl-1,2,3,4,5,6,7,8-octahydro-2-naphthalene nitrile
  • 8,8-dimethyl-1,2,3,4,5,6,7,8-octahydronaphthalene-2-carbonitrile
  • 8,8-dimethyl-2,3,4,5,6,7-hexahydro-1H-naphthalene-2-carbonitrile
  • 2-naphthalenecarbonitrile, 1,2,3,4,5,6,7,8-octahydro-8,8-dimethyl-
  • 1,2,3,4,5,6,7,8-octahydro-8,8-dimethyl naphthalene-2-carbonitrile
  • 1,2,3,4,5,6,7,8-octahydro-8,8-dimethyl-2-naphthalene carbonitrile
  • 1,2,3,4,5,6,7,8-octahydro-8,8-dimethyl-2-naphthalenecarbonitrile
  • 1,2,3,4,5,6,7,8-octahydro-8,8-dimethyl-2-naphthonitrile
  • 1,2,3,4,5,6,7,8-octahydro-8,8-dimethylnaphthalene-2-carbonitrile
  • 8,8-dimethyl-2,3,4,5,6,7-hexahydro-1H-naphthalene-2-carbonitrile
  • 2-Naphthalenecarbonitrile, 1,2,3,4,5,6,7,8-octahydro-8,8-dimethyl-
  • 1,2,3,4,5,6,7,8-Octahydro-8,8-dimethyl-2-naphthalenecarbonitrile
  • 8,8-Dimethyl-1,2,3,4,5,6,7,8-octahydro-2-naphthonitrile
  • 1,2,3,4,5,6,7,8-Octahydro-8,8-dimethyl-2-naphthonitrile

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Seqens

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 189.30143737793
Boiling Point 305 to 307°C @ 760 mm Hg
Vapor Pressure 0.001 mmHg @ 25 °C
Flash Point TCC Value 93.33 °C TCC
logP (o/w) 3.895 est
Solubility
alcohol Yes
water, 4.681 mg/L @ 25 °C (est) Yes
water No
Stability
alkalis Unspecified

Organoleptic Properties

Odor Type: Citrus
citrus, marine, earthy, orris
Odor strength medium , recommend smelling in a 10.00 % solution or less
Substantivity 16 hour(s) at 100.00 %
General comment At 10.00 % in dipropylene glycol. citrus marine earthy

Potential Uses

Applications
Odor purposes Leather , Powder , Spice , Tobacco , Woody
Cosmetic purposes Perfuming agents

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 marine nitrile usage levels up to:
0.8000 % in the fragrance concentrate.
Recommendation for marine nitrile flavor usage levels up to:
not for flavor use.

Safety references

EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):72928-51-9
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :166374
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
8,8-dimethyl-2,3,4,5,6,7-hexahydro-1H-naphthalene-2-carbonitrile
Chemidplus:0072928519