Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:11:05 UTC |
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Update date | 2019-11-26 03:09:32 UTC |
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Primary ID | FDB014115 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | (±)-Limonene |
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Description | Polylimonene, also known as (+/-)-limonene or cajeputene, belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Based on a literature review a significant number of articles have been published on Polylimonene. |
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CAS Number | 9003-73-0 |
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Structure | |
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Synonyms | Synonym | Source |
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(+-)-(RS)-Limonene | ChEBI | (+/-)-limonene | ChEBI | 1,8-p-Menthadiene | ChEBI | 1-Methyl-4-(1-methylethenyl)cyclohexene | ChEBI | 4-Isopropenyl-1-methylcyclohexene | ChEBI | Cajeputene | ChEBI | Dipentene | ChEBI | DL-Limonene | ChEBI | Kautschin | ChEBI | Limonene | Kegg | (+/-)-P-mentha-1,8-diene homopolymer | HMDB | Cyclohexene, 1-methyl-4-(1-methylethenyl)-, homopolymer | HMDB | Dipentene polymer | HMDB | Dipentene, homopolymer | HMDB | Limonene polymer | HMDB | P-Mentha-1,8-diene, homopolymer (7ci) | HMDB | P-Mentha-1,8-diene, polymers (8ci) | HMDB | Polydipentene | HMDB | (D)-Limonene | MeSH, HMDB | AISA 5203-L (+)limonene | MeSH, HMDB | (4S)-1-Methyl-4-isopropenylcyclohex-1-ene | MeSH, HMDB | D-Limonene | MeSH, HMDB | Limonene, (R)-isomer | MeSH, HMDB | (-)-Limonene | MeSH, HMDB | 4-Mentha-1,8-diene | MeSH, HMDB | (+)-Limonene | MeSH, HMDB | Limonene, (+-)-isomer | MeSH, HMDB | Limonene, (S)-isomer | MeSH, HMDB | (+)-(R)-4-Isopropenyl-1-methylcyclohexene | MeSH | (4R)-1-Methyl-4-(1-methylethenyl)cyclohexene | MeSH | (R)-(+)-Limonene | MeSH | (R)-4-Isopropenyl-1-methylcyclohexene | MeSH | D Limonene | MeSH | 4 Mentha 1,8 diene | MeSH | (+-)-Dipentene | manual | (+-)-Limonene | manual | (±)-Dipentene | manual | (±)-Limonene | manual | (R/S)-Limonene | manual |
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Predicted Properties | |
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Chemical Formula | C10H16 |
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IUPAC name | 1-methyl-4-(prop-1-en-2-yl)cyclohex-1-ene |
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InChI Identifier | InChI=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4,10H,1,5-7H2,2-3H3 |
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InChI Key | XMGQYMWWDOXHJM-UHFFFAOYSA-N |
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Isomeric SMILES | CC(=C)C1CCC(C)=CC1 |
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Average Molecular Weight | 136.238 |
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Monoisotopic Molecular Weight | 136.125200515 |
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Classification |
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Description | Belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. |
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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 | Menthane monoterpenoids |
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Alternative Parents | |
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Substituents | - P-menthane monoterpenoid
- Monocyclic monoterpenoid
- Branched unsaturated hydrocarbon
- Cycloalkene
- Cyclic olefin
- Unsaturated aliphatic hydrocarbon
- Unsaturated hydrocarbon
- Olefin
- Hydrocarbon
- Aliphatic homomonocyclic compound
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Molecular Framework | Aliphatic homomonocyclic compounds |
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External Descriptors | |
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Ontology |
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Ontology | No ontology term |
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Physico-Chemical Properties - Experimental |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Not Available | |
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Physical Description | Not Available | |
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Mass Composition | C 88.16%; H 11.84% | DFC |
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Melting Point | < 25 oC | |
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Boiling Point | Bp 178° | DFC |
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Experimental Water Solubility | Not Available | |
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Experimental logP | Not Available | |
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Experimental pKa | Not Available | |
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Isoelectric point | Not Available | |
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Charge | Not Available | |
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Optical Rotation | Not Available | |
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Spectroscopic UV Data | Not Available | |
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Density | Not Available | |
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Refractive Index | Not Available | |
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Spectra |
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Spectra | |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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EI-MS | Mass Spectrum (Electron Ionization) | splash10-014l-9100000000-498293086493b60c2094 | 2015-03-01 | View Spectrum | GC-MS | Polylimonene, non-derivatized, GC-MS Spectrum | splash10-0006-9300000000-132287e3db63dda49102 | Spectrum | GC-MS | Polylimonene, non-derivatized, GC-MS Spectrum | splash10-00kf-9300000000-d7348db845e3e79845dd | Spectrum | Predicted GC-MS | Polylimonene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0006-9200000000-df40612bbf371089d7ac | Spectrum | Predicted GC-MS | Polylimonene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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MS/MS | LC-MS/MS Spectrum - 35V, Positive | splash10-0a4o-9000000000-893d8151186383a89b6a | 2021-09-20 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000i-2900000000-bce8f8616cfd3b16cac9 | 2016-08-02 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-000i-9600000000-583a2621a826cedbca61 | 2016-08-02 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-1000-9100000000-d78cd6fbdd7a13fe9dfa | 2016-08-02 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000i-0900000000-2950ad058f77d7bc9f76 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-000i-0900000000-6f48f3b0b500d4f25ec9 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-014r-5900000000-1c30c00bfa4058f5e22b | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-001a-9400000000-fb09a1cdd4bc09480281 | 2021-09-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0564-9000000000-dc5effa7f00987fc8567 | 2021-09-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-00mo-9000000000-40d99aa482e2ce5a66f1 | 2021-09-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000i-0900000000-a013b4ae27f975ab5621 | 2021-09-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-000i-0900000000-a013b4ae27f975ab5621 | 2021-09-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-014i-8900000000-d835e92fba2c2a238797 | 2021-09-25 | View Spectrum |
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NMR | |
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External Links |
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ChemSpider ID | 20939 |
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ChEMBL ID | Not Available |
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KEGG Compound ID | C06078 |
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Pubchem Compound ID | 22311 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | Not Available |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | Not Available |
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HMDB ID | HMDB32473 |
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CRC / DFC (Dictionary of Food Compounds) ID | JFH51-A:JNZ87-F |
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EAFUS ID | 2036 |
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Dr. Duke ID | DL-LIMONENE|DIPENTENE |
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BIGG ID | Not Available |
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KNApSAcK ID | C00003043 |
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HET ID | Not Available |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | rw1240221 |
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SuperScent ID | Not Available |
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Wikipedia ID | Limonene |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Food | Content Range | Average | Reference |
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Food | | | Reference |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | Descriptor | ID | Definition | Reference |
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allergenic | 50904 | A chemical compound which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy. | DUKE | anti bacterial | 33282 | A substance that kills or slows the growth of bacteria. | DUKE | anti viral | 22587 | A substance that destroys or inhibits replication of viruses. | DUKE | expectorant | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | irritant | | | DUKE | pesticide | 25944 | Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests. | DUKE | sedative | 35717 | A central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety. | DUKE |
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Enzymes | Not Available |
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Pathways | Not Available |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Flavor | Citations |
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citrus |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| herbal |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| terpene |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| camphor |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
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Files |
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MSDS | Not Available |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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Content Reference | — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004). — Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
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