geranyl benzoate
trans-3,7-dimethyl-2,6-octadien-1-yl benzoate
Identification
| Name | geranyl benzoate |
| IUPAC | [(2E)-3,7-dimethylocta-2,6-dienyl] benzoate |
| EINECS | 202-337-0 |
| FDA UNII | B4M42WH83V |
| Molecular Formula | C17 H22 O2 |
| Molecular Weight | 258.36074000 |
| MDL Number | MFCD00036513 |
| Nikkaji Number | J60.346E |
| Beilstein | 3119464 |
| CoE Number | 639 |
Regulatory
| JECFA Food Flavoring | 860 geranyl benzoate |
| DG SANTE Food Flavourings | 09.767 geranyl benzoate |
| FEMA Number | 2511 |
| FDA | No longer provide for the use of these seven synthetic flavoring substances |
| FDA Mainterm (SATF) | 94-48-4 ; GERANYL BENZOATE |
| FDA Regulation | FDA PART 172 -- FOOD ADDITIVES PERMITTED FOR DIRECT ADDITION TO FOOD FOR HUMAN CONSUMPTION |
Physical Properties
| Appearance | colorless to yellow clear oily liquid (est) |
| Assay | 95.00 to 100.00 sum of isomers |
| Equivalence Factor for Assay | 129.08 |
| Food Chemicals Codex Listed | Yes |
| Specific Gravity | 0.98300 to 0.98900 @ 25.00 °C. |
| Pounds per Gallon - (est). | 8.180 to 8.229 |
| Refractive Index | 1.51600 to 1.52100 @ 20.00 °C. |
| Boiling Point | 305.00 °C. @ 760.00 mm Hg, 198.00 to 200.00 °C. @ 15.00 mm Hg |
| Acid Value | 1.00 max. KOH/g |
| Vapor Pressure | 0.000017 mmHg @ 25.00 °C. (est) |
| Flash Point | 230.00 °F. TCC ( 110.00 °C. ) |
| logP (o/w) | 5.705 (est) |
| Soluble in | alcohol |
| Insoluble in | water |
Cosmetic Information
| CosIng | cosmetic data |
| Cosmetic Uses | perfuming agents |
Organoleptic Properties
| Odor Strength | medium |
| Substantivity | > 8 hour(s) at 100.00 % |
| Odor Description |
at 100.00 %. Long-lasting rose, amber
|
| Taste Description | amber |
Safety Information
| Preferred SDS | View |
| European information | Most important hazard(s): |
| Human Experience | 2 % solution: no irritation or sensitization. |
| Oral/Parenteral Toxicity | oral-rat LD50 > 5000 mg/kg |
| Dermal Toxicity | skin-rabbit LD50 > 5000 mg/kg |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | flavor and fragrance agents |
| RIFM Fragrance Material Safety Assessment | Search |
| limits in the finished product for - "leave on the skin contact" | 0.5000 % Recommendation. |
| limits in the finished product for - "wash off the skin contact" | 0.5000 % Recommendation. |
| limits in the finished product for - "no skin contact" | 4.0000 % Recommendation. |
| Recommendation for geranyl benzoate usage levels up to | 4.0000 % in the fragrance concentrate. |
| Maximised Survey-derived Daily Intakes (MSDI-EU) | 3.40 (μg/capita/day) |
| Maximised Survey-derived Daily Intakes (MSDI-USA) | 0.03 (μg/capita/day) |
| Structure Class | I |
| baked goods | - |
| beverages(nonalcoholic) | 0.10000 |
| beverages(alcoholic) | - |
| breakfast cereal | - |
| cheese | - |
| chewing gum | - |
| condiments / relishes | - |
| confectionery froastings | - |
| egg products | - |
| fats / oils | - |
| fish products | - |
| frozen dairy | 0.16000 |
| fruit ices | 0.16000 |
| gelatins / puddings | - |
| granulated sugar | - |
| gravies | - |
| hard candy | - |
| 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 | - |
BOC Sciences
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Potential Uses
Natural Occurrence
Synonyms
benzoic acid geraniol ester
benzoic acid geranyl ester
benzoic acid, geraniol ester
dimethyl-2,6-octadien-1-yl benzoate
(E)-3,7-
dimethyl-2,6-octadien-1-yl benzoate
trans-3,7-
dimethyl-2,6-octadien-1-yl benzoate
(E)-3,7-
dimethyl-2,6-octadiene-1-yl benzoate
(2E)-3,7-
dimethyl-2,6-octadienyl benzoate
(2E)-3,7-
dimethylocta-2,6-dien-1-yl benzoate
3,7-
dimethylocta-2,6-dienyl benzoate
[(2E)-3,7-
dimethylocta-2,6-dienyl] benzoate
geraniol benzoate
(E)-
geranyl benzoate
geranyl benzoate S
(E)-
neryl benzoate
2,6-
octadien-1-ol, 3,7-dimethyl-, benzoate, (2E)-
2,6-
octadien-1-ol, 3,7-dimethyl-, benzoate, (E)-
PubMed:
In vivo anti-inflammatory activity of some naturally occurring O- and N-prenyl secondary metabolites.
PubMed:
Antiherbivore prenylated benzoic acid derivatives from Piper kelleyi.
PubMed:
Synthesis of 3-farnesyl salicylic acid, a novel antimicrobial from Piper multiplinervium.
PubMed:
Structural characterization of amorfrutins bound to the peroxisome proliferator-activated receptor γ.
PubMed:
Cloning and expression analysis of ten genes associated with picrosides biosynthesis in Picrorhiza kurrooa.
PubMed:
Contact and fumigant toxicity of Pinus densiflora needle hydrodistillate constituents and related compounds and efficacy of spray formulations containing the oil to Dermatophagoides farinae.
PubMed:
Sodium benzoate, a metabolite of cinnamon and a food additive, upregulates neuroprotective Parkinson disease protein DJ-1 in astrocytes and neurons.
PubMed:
Expression of 3-hydroxy-3-methylglutaryl-CoA reductase, p-hydroxybenzoate-m-geranyltransferase and genes of phenylpropanoid pathway exhibits positive correlation with shikonins content in arnebia [Arnebia euchroma (Royle) Johnston].
PubMed:
Activation of the human transient receptor potential vanilloid subtype 1 by essential oils.
PubMed:
Geranylation of benzoic acid derivatives by enzymatic extracts from Piper crassinervium (Piperaceae).
PubMed:
W7FW14F apomyoglobin amyloid aggregates-mediated apoptosis is due to oxidative stress and AKT inactivation caused by Ras and Rac.
PubMed:
Functional characterization of LePGT1, a membrane-bound prenyltransferase involved in the geranylation of p-hydroxybenzoic acid.
PubMed:
Biosynthetic origins of the isoprene units of gaudichaudianic acid in Piper gaudichaudianum (Piperaceae).
PubMed:
Isolation and structural determination of xerophytolic acid A, a 3-geranyl-4-hydroxybenzoate derivative from Xerophyta plicata.
PubMed:
In-vitro human skin penetration of the fragrance material geranyl nitrile.
PubMed:
Functional characterization of OsPPT1, which encodes p-hydroxybenzoate polyprenyltransferase involved in ubiquinone biosynthesis in Oryza sativa.
PubMed:
Geranyl N-dimethylallylanthranilate, a new compound from Esenbeckia yaaxhokob.
PubMed:
Electroantennographic and behavioral responses of the sphinx moth Manduca sexta to host plant headspace volatiles.
PubMed:
Novel anti-inflammatory compounds from Myrsine seguinii, terpeno-benzoic acids, are inhibitors of mammalian DNA polymerases.
PubMed:
Chemicals in laboratory room air stimulate olfactory neurons of female Bombyx mori.
PubMed:
3-Geranyl-4-hydroxy-5-(3'-methyl-2'-butenyl)benzoic acid as an anti-inflammatory compound from Myrsine seguinii.
PubMed:
Kinetics of Cdc42 membrane extraction by Rho-GDI monitored by real-time fluorescence resonance energy transfer.
PubMed:
Stringent structural requirements for anti-Ras activity of S-prenyl analogues.
PubMed:
Isoprenyl phenyl ethers from liverworts of the genus Trichocolea: cytotoxic activity, structural corrections, and synthesis.
PubMed:
Floral Scent Production in Clarkia (Onagraceae) (I. Localization and Developmental Modulation of Monoterpene Emission and Linalool Synthase Activity).
PubMed:
Characterization and mechanism of (4S)-limonene synthase, a monoterpene cyclase from the glandular trichomes of peppermint (Mentha x piperita).
PubMed:
Effects of olfactory stimulation with jasmin and its component chemicals on the duration of pentobarbital-induced sleep in mice.
PubMed:
Mechanism of the pyrophosphate migration in the enzymatic cyclization of geranyl and linalyl pyrophosphates to (+)- and (-)-bornyl pyrophosphates.
PubMed:
Investigation of isoprenoid benzoates and naphthoates by reversed-phase liquid chromatography. Isocratic elution characteristics of benzoates and naphthoates of C5-C20 terpenoid alcohols.
PubMed:
Biosynthesis of monoterpenes: preliminary characterization of bornyl pyrophosphate synthetase from sage (Salvia officinalis) and demonstration that Geranyl pyrophosphate is the preferred substrate for cyclization.
PubMed:
Formation of 3-hexaprenyl-4-hydroxybenzoate by matrix-free mitochondrial membrane-rich preparations of yeast.
PubMed:
Purification and characterization of two forms of geranyl transferase from Ricinus communis.
PubMed:
3-Hydroxy-3-methylglutaryl CoA reductase and mevalonate kinase of Neurospora crassa.
PubMed:
The purification and properties of pig liver geranyl pyrophosphate synthetase.