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gamma-nonalactone (aldehyde C-18 (so-called))

Chemical Structure

General Material Information

Preferred name gamma-nonalactone (aldehyde C-18 (so-called))
Trivial Name (±)-γ-Nonalactone
Short Description nonano-1,4-lactone
Formula C9 H16 O2
CAS Number 104-61-0
FEMA Number 2781
Flavis Number 10.001
ECHA Number 203-219-1
FDA UNII I1XGH66S8P
Nikkaji Number J2.412K
MDL MFCD00005403
COE Number 178
Bio Activity Summary External link
NMR Predictor External link
JECFA Food Flavoring 229 gamma-nonalactone
FDA Patent No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm 104-61-0 ; GAMMA-NONALACTONE
Synonyms
  • abricolin
  • aldehyde C-18
  • aldehyde C-18 (gamma-nonalactone)
  • aldehyde C-18 (so-called)
  • aldehyde C-18 chiral natural
  • aldehyde C-18 FCC
  • aldehyde C-18 natural
  • aldehyde C18
  • aldehyde C18 so-called
  • delta-N- amyl butyrolactone
  • gamma- amyl butyrolactone
  • gamma-N- amyl butyrolactone
  • 4-amyl-4-hydroxybutyric acid lactone
  • 4-N- amyl-4-hydroxybutyric acid lactone
  • gamma- amyl-gamma-butyrolactone
  • d-n- amylbutyrolactone
  • apricolin
  • C-18 aldehyde
  • coconut aldehyde
  • dihydro-5-pentyl-2(3H)-furanon
  • dihydro-5-pentyl-2(3H)-furanone
  • 4-hydroxynonanoic acid gamma-lactone
  • 4-nonalactone
  • gamma- nonalactone (aldehyde C-18 (so-called))
  • gamma- nonalactone (aldehyde C-18)
  • gamma- nonalactone (C-18)
  • gamma- nonalactone (coconut aldehyde)
  • GAMMA nonalactone (coconut aldehyde)
  • gamma- nonalactone FCC
  • gamma- nonalactone natural
  • gamma- nonalactone, nature-identical
  • 1,4-nonalolide
  • nonan-1,4-olide
  • nonan-4-olide
  • nonano-1,4-lactone
  • nonanoic acid, 4-hydroxy-, gamma-lactone
  • gamma- nonanolactone
  • 1,4-nonanolide
  • 4-nonanolide
  • g- nonanolide
  • gamma- nonanolide
  • nonanolide-1,4
  • 1,4-nonyl lactone
  • gamma- nonyl lactone
  • gamma- nonyl-gamma-butylrolactone
  • gamma- nonylactone
  • gamma- pelargolactone
  • 4-pentyl butan-4-olide
  • 4-pentyl butanolide
  • 4-pentyl-butanolide
  • 5-pentyl-dihydro-furan-2-one
  • g- pentyl-g-butyrolactone
  • gamma- pentyl-gamma-butyrolactone
  • 4-pentylbutan-4-olide
  • 5-pentyldihydro-2(3H)-furanone
  • 5-pentyldihydrofuran-2(3H)-one
  • 5-pentyloxolan-2-one
  • prunolide
  • 5-pentyloxolan-2-one
  • 2(3H)-Furanone, dihydro-5-pentyl-
  • Nonanoic acid, 4-hydroxy-, γ-lactone
  • γ-n-Amylbutyrolactone
  • γ-Amyl-γ-butyrolactone
  • γ-Nonalactone
  • γ-Nonanolide
  • γ-Amylbutyrolactone
  • 4-Nonanolide
  • 4-Hydroxynonanoic acid lactone
  • γ-Nonanolactone
  • 4-Pentyl-butanolide
  • γ-Pentyl-γ-butyrolactone
  • Cocos aldehyde
  • 5-Pentyldihydro-2(3H)-furanone
  • (±)-4-n-Pentylbutyrolactone
  • (RS)-γ-Nonalactone
  • (±)-γ-Nonalactone
  • NSC 24253
  • NSC 46099
  • 4-Pentylbutan-4-olide
  • Nonyl lactone
  • 5-Pentyltetrahydrofuran-2-one

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

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Literature & References

Leffingwell:Chirality or Article
5-pentyloxolan-2-one
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:104-61-0
Pubchem (cid):7710
Pubchem (sid):134972886
Flavornet:104-61-0
Pherobase:View
Publications by PubMed
Chemical composition and aroma evaluation of essential oils from Evolvulus alsinoides L.
6-Pentyl-2H-pyran-2-one: a potent peach-derived kairomone for New Zealand flower thrips, Thrips obscuratus.
Aroma characterization of chinese rice wine by gas chromatography-olfactometry, chemical quantitative analysis, and aroma reconstitution.
Identification of characteristic flavour precursors from enzymatic hydrolysis-mild thermal oxidation tallow by descriptive sensory analysis and gas chromatography-olfactometry and partial least squares regression.
Effect of α-tocopherol on lactone formation in marbled beef and changes in lactone volatility during storage.
Volatile composition and sensory properties of Vitis vinifera red cultivars from north west Spain: correlation between sensory and instrumental analysis.
Minimal structural requirements of alkyl γ-lactones capable of antagonizing the cocaine-induced motility decrease in planarians.
Effects of alpha-tocopherol on lactones in beef headspace during storage.
Analytical and sensorial characterization of the aroma of wines produced with sour rotten grapes using GC-O and GC-MS: identification of key aroma compounds.
Volatile compounds and the changes in their concentration levels during storage in beers containing varying malt concentrations.
Odor-active compounds in cardboard.
Fate of key odorants in Sauternes wines through aging.
Screening for gamma-nonalactone in the headspace of freshly cooked non-scented rice using SPME/GC-O and SPME/GC-MS.
Odor detection thresholds and enantiomeric distributions of several 4-alkyl substituted gamma-lactones in Australian red wine.
Quantification of several 4-alkyl substituted gamma-lactones in Australian wines.
Analysis of volatile compounds in beef fat by dynamic-headspace solid-phase microextraction combined with gas chromatography-mass spectrometry.
Identification of volatile compounds responsible for prune aroma in prematurely aged red wines.
Aroma components of American country ham.
Characterization of the key aroma compounds in apricots (Prunus armeniaca) by application of the molecular sensory science concept.
Astrocytic biotransformation of trans-4-hydroxy-2-nonenal is dose-dependent.
Aroma composition of red wines by different extraction methods and Gas Chromatography-SIM/MASS spectrometry analysis.
On-line reversed-phase liquid chromatography-gas chromatography coupled to mass spectrometry for enantiomeric analysis of chiral compounds in fruit beverages.
Senescence marker protein-30 is a unique enzyme that hydrolyzes diisopropyl phosphorofluoridate in the liver.
Characterization of the aroma of a wine from maccabeo. Key role played by compounds with low odor activity values.
Characterization of odor-active compounds in Californian chardonnay wines using GC-olfactometry and GC-mass spectrometry.
How low pH can intensify beta-damascenone and dimethyl trisulfide production through beer aging.
Use of GC-olfactometry to identify the hop aromatic compounds in beer.
Lipase-catalysed resolution of gamma- and delta-lactones.
Chirality of the gamma-lactones produced by Sporidiobolus salmonicolor grown in two different media.

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
FDA Substances Added to Food (formerly EAFUS):View
CHEBI:View
CHEMBL:View
KEGG (GenomeNet):C08501
HMDB (The Human Metabolome Database):HMDB31531
FooDB:FDB008395
YMDB (Yeast Metabolome Database):YMDB01623
Export Tariff Code:2932.20.5050
Typical G.C.
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
EFSA Update of results on the monitoring of furan levels in food:Read Report
EFSA Previous report: Results on the monitoring of furan levels in food:Read Report
EFSA Report of the CONTAM Panel on provisional findings on furan in food:Read Report
Formulations/Preparations:
•assay: 97% minimum (98%). •technical, fcc

Suppliers

ACS International Advanced Biotech
Ambles Nature et Chimie Anhui Haibei
Artiste Associate Allied Chemicals
Augustus Oils Aurochemicals
Beijing Lys Chemicals Bell Flavors & Fragrances
Berjé BeYonde
BOC Sciences Charkit Chemical
Citrus and Allied Essences CJ Latta & Associates
Creatingperfume.com De Monchy Aromatics
Diffusions Aromatiques ECSA Chemicals
Elan Inc. Ernesto Ventós
Excellentia International ExtraSynthese
Fleurchem Frey + Lau
H. Interdonati, Inc. IFF
Indukern F&F Inoue Perfumery
Jiangyin Healthway K.L. Koh Enterprise
Kao Corporation Kingchem Laboratories
Kun Shan P&A Lluch Essence
M&U International Mane
Moellhausen Odowell Co.,ltd
OQEMA Organica Aromatics
PCW France Pearlchem Corporation
Pell Wall Perfumes Penta International
PerfumersWorld Perfumery Laboratory
Phoenix Aromas & Essential Oils Primechem
Prinova Quimdis
R C Treatt & Co Ltd Reincke & Fichtner
Riverside Aromatics Sigma-Aldrich
Soda Aromatic SRS Aromatics
Sunaux International Symrise
SysKem Chemie Taytonn ASCC
TCI AMERICA Tengzhou Xiang Yuan Aroma Chemicals
The John D. Walsh Company The Lermond Company
The Perfumers Apprentice Ungerer & Company
United International Vigon International
WEN International WholeChem
ACS International GmbH Advanced Biotech. Inc.
Augustus Oils Ltd Beijing Lys Chemicals Co, LTD.
Berje Inc. Charkit Chemical Corporation
CJ Latta & Associates, LLC Fleurchem, Inc.
Indukern, S.A. F&F Ingredients Division Jiangyin Healthway International Trade Co., Ltd
Lluch Essence S.L. M&U International LLC
Moellhausen S.P.A. Penta International Corporation
PerfumersWorld Ltd. Anhui Primechem Co., Ltd.
Riverside Aromatics Ltd. Soda Aromatic Co., Ltd.
SRS Aromatics Ltd Symrise AG
Taytonn ASCC Pte Ltd The John D. Walsh Company, Inc
R C Treatt and Co Ltd Qingdao Free Trade Zone United International Co Ltd
Ernesto Ventós S.A. WholeChem, LLC

PhysChem Properties

Material listed in food chemical codex Yes
Molecular weight 156.22491455078
Specific gravity @ 25 °C
Pounds per Gallon 7.972 to 8.03
Specific gravity @ 20 °C
Pounds per Gallon 7.997 to 8.081
Refractive Index 1.446 to 1.449 @ 20 °C
Boiling Point 121 to 122°C @ 6 mm Hg
Acid Value 1.2 max KOH/g
Vapor Pressure 0.009 mmHg @ 25 °C
Vapor Density 1
Flash Point TCC Value 113 °C TCC
logP (o/w) 1.942 est
Shelf life 24 months (or longer if stored properly.)
Storage notes Store in cool, dry place in tightly sealed containers, protected from heat and light.
Solubility
benzyl alcohol Yes
dipropylene glycol Yes
ethyl alcohol, 1:2 in 60% alcohol Yes
ethyl alcohol, 1:5 in 50% alcohol Yes
fixed oils Yes
paraffin oil Yes
propylene glycol Yes
water, 1201 mg/L @ 25 °C (est) Yes
Stability
cream Unspecified
detergent Unspecified
hair spray Unspecified
lipstick Unspecified
lotion Unspecified
non-discoloring in most media Unspecified
powder Unspecified
soap Unspecified

Organoleptic Properties

Odor Type: Coconut
coconut, creamy, waxy, sweet, buttery, oily, fatty
Odor strength medium
Substantivity 309 hour(s) at 100.00 %
Luebke, William tgsc, (1982) At 100.00 %. coconut creamy waxy sweet buttery oily
Mosciano, Gerard P&F 17, No. 1, 41, (1992) Sweet, creamy, coconut, fatty with oily buttery nuances
Flavor Type: Coconut
coconut, creamy, waxy, fatty, milky
Mosciano, Gerard P&F 17, No. 1, 41, (1992) At 10.00 ppm. Coconut, creamy, waxy with fatty milky notes
Used in coconut, peach, apricot, vanilla, maple, honey and chocolate flavors. Creamy
Useful in: brown nuts, brown cocoa, brown others, dairy, vanilla, fruity red, fruity yellow, fruity tropical, sweet others, alcoholics. Tending towards coconut, cream and apricot
General comment Fat, cocoa, apricot

Occurrences

Safety Information

Safety information

Preferred SDS: View
European information :
Most important hazard(s):
Xi - Irritant
R 36/38 - Irritating to skin and eyes.
S 02 - Keep out of the reach of children.
S 24/25 - Avoid contact with skin and eyes.
S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S 36 - Wear suitable protective clothing.
Hazards identification
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
Acute toxicity, Oral (Category 4), H302
GHS Label elements, including precautionary statements
Pictogramexclamation-mark.jpg
Signal word Warning
Hazard statement(s)
H302 - Harmful if swallowed
Precautionary statement(s)
P264 - Wash skin thouroughly after handling.
P270 - Do not eat, drink or smoke when using this product.
P301 + P312 - IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P330 - Rinse mouth.
P501 - Dispose of contents/ container to an approved waste disposal plant.
Human Experience:
10 % solution: no irritation or sensitization.
Oral/Parenteral Toxicity:
gavage-rat LD50 [sex: M,F] 9780 mg/kg
(Jenner et al., 1964)

oral-rat LD50 [sex: M] 6600 mg/kg
(Moreno, 1972a)

gavage-guinea pig LD50 [sex: M,F] 3440 mg/kg
(Jenner et al., 1964)

oral-guinea pig LD50 3440 mg/kg
BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS
Food and Cosmetics Toxicology. Vol. 2, Pg. 327, 1964.

oral-rat LD50 6600 mg/kg
Food and Cosmetics Toxicology. Vol. 13, Pg. 889, 1975.

Dermal Toxicity:
skin-rabbit LD50 > 5000 mg/kg
Food and Cosmetics Toxicology. Vol. 13, Pg. 889, 1975.

Inhalation Toxicity:
Not determined

Safety in use information

Category:
cosmetic, flavor and 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 gamma-nonalactone (aldehyde C-18 (so-called)) usage levels up to:
10.0000 % in the fragrance concentrate.
Maximised Survey-derived Daily Intakes (MSDI-EU): 1000.00 (μg/capita/day)
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: 3
Click here to view publication 3
average usual ppmaverage maximum ppm
baked goods: -55.00000
beverages(nonalcoholic): -11.00000
beverages(alcoholic): --
breakfast cereal: --
cheese: --
chewing gum: -15.00000
condiments / relishes: --
confectionery froastings: -25.00000
egg products: --
fats / oils: --
fish products: --
frozen dairy: -14.00000
fruit ices: -14.00000
gelatins / puddings: -28.00000
granulated sugar: --
gravies: --
hard candy: -33.00000
imitation dairy: --
instant coffee / tea: --
jams / jellies: --
meat products: --
milk products: --
nut products: --
other grains: --
poultry: --
processed fruits: --
processed vegetables: --
reconstituted vegetables: --
seasonings / flavors: --
snack foods: --
soft candy: --
soups: --
sugar substitutes: --
sweet sauces: --

Safety references

European Food Safety Athority(EFSA):Flavor usage levels; Subacute, Subchronic, Chronic and Carcinogenicity Studies; Developmental / Reproductive Toxicity Studies; Genotoxicity Studies...

European Food Safety Authority (EFSA) reference(s):

Opinion of the Scientific Panel on Food Additives, Flavourings, Processing Aids and Materials in contact with Food (AFC) on a request from the Commission related to - Flavouring Group Evaluation 10: Aliphatic primary and secondary saturated and unsaturated alcohols, aldehydes, acetals, carboxylic acids and esters containing an additional oxygenated functional group and lactones from chemical groups 9, 13 and 30 - (Commission Regulation (EC) No 1565/2000 of 18 July 2000)
View page or View pdf

Flavouring Group Evaluation 10, Revision 1 (FGE10 Rev1)[1] - Aliphatic primary and secondary saturated and unsaturated alcohols, aldehydes, acetals, carboxylic acids and esters containing an additional oxygenated functional group and lactones from chemical groups 9, 13 and 30 - Scientific Opinion of the Panel on Food Additives, Flavourings, Processing Aids and Materials in Contact with Food (AFC)
View page or View pdf

Flavouring Group Evaluation 64 (FGE.64): Consideration of aliphatic acyclic diols, triols, and related substances evaluated by JECFA (57th meeting) structurally related to aliphatic primary and secondary saturated and unsaturated alcohols, aldehydes, acetals, carboxylic acids and esters containing an additional oxygenated functional group and lactones from chemical groups 9, 13 and 30 evaluated by EFSA in FGE.10Rev1 (EFSA, 2008ab)
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 92 (FGE.92): Consideration of aliphatic acyclic diols, triols, and related substances evaluated by JECFA (68th meeting) structurally related to aliphatic primary and secondary saturated and unsaturated alcohols, aldehydes, acetals, carboxylic acids and esters containing an additional oxygenated functional group and lactones evaluated by EFSA in FGE.10Rev1 (2009)
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 10, Revision 2 (FGE.10Rev2): Aliphatic primary and secondary saturated and unsaturated alcohols, aldehydes, acetals, carboxylic acids and esters containing an additional oxygenated functional group and lactones from chemical groups 9, 13 and 30
View page or View pdf

EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):104-61-0
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :7710
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:1
5-pentyloxolan-2-one
Chemidplus:0000104610
RTECS:LU3675000 for cas# 104-61-0