| Record Information |
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| Version | 1.0 |
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| Creation date | 2015-10-09 22:33:29 UTC |
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| Update date | 2017-01-19 02:36:42 UTC |
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| FoodComEx ID | PC000940 |
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| FoodDB Record | FDB013792 |
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| Chemical Information |
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| Name | Geraniol |
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| Description | beta-Geraniol, also known as (E)-nerol, the isomer of nerol (or geranyl alcohol, is a monoterpenoid alcohol. It belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-eritritol-phosphate (MEP) pathway in the plastids (PMID: 7640522). Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. beta-Geraniol is an isoprenoid lipid molecule that is very hydrophobic, practically insoluble in water, and relatively neutral. beta-Geraniol has a sweet, citrus, and floral taste. beta-Geraniol is found in highest concentrations in common grapes, black walnuts, and common thymes and in lower concentrations in cardamoms, common oregano, and gingers. beta-Geraniol has also been detected in lemon verbena, oval-leaf huckleberries, common pea, sweet cherries, and nopals. This could make beta-geraniol a potential biomarker for the consumption of these foods. It is found in as an alcohol and as its ester in many essential oils including geranium oil. It is the primary part of rose oil, palmarosa oil, and citronella oil (Java type) and occurs in small quantities in geranium, lemon, and many other essential oils. Because it has a rose-like odor, it is commonly used in perfumes. It is used to create flavors such as peach, raspberry, grapefruit, red apple, plum, lime, orange, lemon, watermelon, pineapple, and blueberry. Geraniol is produced by the scent glands of honeybees to mark nectar-bearing flowers and locate the entrances to their hives (http//doi:10.1051/apido:19900403) |
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| CAS Number | 106-24-1 |
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| Structure | |
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| Synonyms | | Synonym | Source |
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| (2E)-3,7-Dimethyl-2,6-octadien-1-ol | biospider | | (2E)-3,7-Dimethylocta-2,6-dien-1-ol | biospider | | (E)-3,7-Dimethyl-2,6-octadien-1-ol | biospider | | (E)-Geraniol | biospider | | (E)-Nerol | biospider | | 2-trans-3,7-Dimethyl-2,6-octadien-1-ol | biospider | | 2-trans-3,7-dimethyl-2,6-octadiene-1-ol | biospider | | 2,6-Octadien-1-ol, 3,7-dimethyl-, (2E)- | biospider | | 2,6-Octadien-1-ol, 3,7-dimethyl-, (E)- | biospider | | 2,6-Octadien-1-ol, 3,7-dimethyl-, trans- | biospider | | 2E-Geraniol | biospider | | 3,7-Dimethyl-(2e)-2,6-octadien-1-ol | HMDB | | 3,7-Dimethyl-(e)-2,6-octadien-1-ol | HMDB | | 3,7-Dimethyl-2,6-octadien-1-ol, (E)- | biospider | | 3,7-Dimethyl-trans-2,6-octadien-1-ol | biospider | | b-Geraniol | db_source | | beta-Geraniol | biospider | | FEMA 2507 | db_source | | Geraniol | db_source | | Geranyl alcohol | db_source | | Lemonol | db_source | | t-Geraniol | ChEBI | | trans-2,6-Dimethyl-2,6-octadien-8-ol | biospider | | trans-3,7-Dimethy- octa-2,6-dien-1-ol | biospider | | trans-3,7-Dimethyl-2,6-octadien-1-ol | biospider | | trans-Geraniol | biospider |
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| Chemical Formula | C10H18O |
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| IUPAC name | (2E)-3,7-dimethylocta-2,6-dien-1-ol |
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| InChI Identifier | InChI=1S/C10H18O/c1-9(2)5-4-6-10(3)7-8-11/h5,7,11H,4,6,8H2,1-3H3/b10-7+ |
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| InChI Key | GLZPCOQZEFWAFX-JXMROGBWSA-N |
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| Isomeric SMILES | CC(C)=CCC\C(C)=C\CO |
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| Average Molecular Weight | 154.253 |
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| Monoisotopic Molecular Weight | 154.1357652 |
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| Chemical Taxonomy |
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| Description | Belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle. |
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| Kingdom | Organic compounds |
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| Super Class | Lipids and lipid-like molecules |
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| Class | Prenol lipids |
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| Sub Class | Monoterpenoids |
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| Direct Parent | Acyclic monoterpenoids |
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| Alternative Parents | |
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| Substituents | - Acyclic monoterpenoid
- Fatty alcohol
- Fatty acyl
- Organic oxygen compound
- Hydrocarbon derivative
- Primary alcohol
- Organooxygen compound
- Alcohol
- Aliphatic acyclic compound
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| Molecular Framework | Aliphatic acyclic compounds |
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| External Descriptors | |
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| Physico-Chemical Properties - Experimental |
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| Property | Value | Reference |
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| Experimental logP | 3.56 | GRIFFIN,S ET AL. (1999) |
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| Experimental Water Solubility | 0.1 mg/mL at 25 oC | CHEMICALS INSPECTION AND TESTING INSTITU (1992) |
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| Melting Point | <-15 oC | |
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| Foods of Origin |
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| Food | Content Range | Average | Reference |
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| Food | | | Reference |
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| Production Data |
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| Production Method | commercial |
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| Production Method Reference | Not Available |
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| Production Method Reference File | Not Available |
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| Quantity Available | Production upon request, up to 4 g |
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| Delivery Time | Not Available |
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| Storage Form | liquid |
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| Storage Conditions | -80°C |
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| Stability | Not Available |
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| Purity | Not Available |
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| Spectra |
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| Spectral Data Upon Request | Not Available |
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| Provider Information |
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| Commercial Vendors |
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| AKSci | G461 |
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| Toronto Research Chemicals | G367000 |
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