| Record Information |
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| Version | 1.0 |
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| Creation date | 2010-04-08 22:10:47 UTC |
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| Update date | 2019-11-26 03:08:36 UTC |
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| Primary ID | FDB013567 |
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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 | 138-86-3 |
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| Structure | |
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| Synonyms | | Synonym | Source |
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| Not Available | Not Available |
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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 |
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| Physico-Chemical Properties - Experimental | | Property | Value | Reference |
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| Physical state | liquid | |
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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 | -95 oC | |
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| Boiling Point | Not Available | |
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| Experimental Water Solubility | 0.00757 mg/mL at 25 oC | MILLER,DJ & HAWTHORNE,SB (2000A) |
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| Experimental logP | 4.57 | LI,J & PERDUE,EM (1995) |
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| Experimental pKa | Not Available | |
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| Isoelectric point | Not Available | |
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| Charge | 0 | |
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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 | Not Available |
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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 | 15384 |
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| Phenol-Explorer ID | Not Available |
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| DrugBank ID | Not Available |
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| HMDB ID | Not Available |
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| CRC / DFC (Dictionary of Food Compounds) ID | JFH51-A:JFH51-A |
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| EAFUS ID | Not Available |
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| Dr. Duke ID | LIMONENE|CARVENE |
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| BIGG ID | 47361 |
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| KNApSAcK ID | C00000823 |
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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 | 138-86-3 |
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| GoodScent ID | Not Available |
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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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| acaricide | 22153 | A substance used to destroy pests of the subclass Acari (mites and ticks). | DUKE | | acetylcholinesterase inhibitor | 38462 | An EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that interferes with the action of enzyme acetylcholinesterase (EC 3.1.1.7), which helps breaking down of acetylcholine into choline and acetic acid. | DUKE | | allelochemic | | | DUKE | | 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 acetylcholinesterase | 38462 | An EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that interferes with the action of enzyme acetylcholinesterase (EC 3.1.1.7), which helps breaking down of acetylcholine into choline and acetic acid. | DUKE | | anti adenomic | 35610 | A substance that inhibits or prevents the proliferation of neoplasms. | DUKE | | anti Alzheimeran | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | | anti asthmatic | 49167 | A drug used to treat asthma. | DUKE | | anti bacterial | 33282 | A substance that kills or slows the growth of bacteria. | DUKE | | anti cancer | 35610 | A substance that inhibits or prevents the proliferation of neoplasms. | DUKE | | anti esophagitic | | | DUKE | | anti feedant | | | DUKE | | anti flu | 22587 | A substance that destroys or inhibits replication of viruses. | DUKE | | anti inflammatory | 35472 | A substance that reduces or suppresses inflammation. | DUKE | | anti lithic | | | DUKE | | anti lymphomic | | | DUKE | | anti metastatic | 35610 | A substance that inhibits or prevents the proliferation of neoplasms. | DUKE | | anti mutagenic | | | DUKE | | anti obesity | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | | anti septic | 33281 | A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans. | DUKE | | anti spasmodic | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | | antitumor | 35610 | A substance that inhibits or prevents the proliferation of neoplasms. | DUKE | | anti viral | 22587 | A substance that destroys or inhibits replication of viruses. | DUKE | | apoptotic | | | DUKE | | bronchoprotectant | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | | cancer preventive | 35610 | A substance that inhibits or prevents the proliferation of neoplasms. | DUKE | | candidistat | | | DUKE | | chemopreventive | 35610 | A substance that inhibits or prevents the proliferation of neoplasms. | DUKE | | cholesterolytic | | | DUKE | | cytochrome-p450 inducer | | | DUKE | | detoxicant | 50247 | Any protective agent counteracting or neutralizing the action of poisons. | DUKE | | enterocontractant | | | DUKE | | expectorant | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | | flavor | 48318 | A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell. | DUKE | | fungiphilic | | | DUKE | | fungistat | | | DUKE | | glutathione-S-transferase inducer | | | DUKE | | herbicide | 24527 | A substance used to destroy plant pests. | DUKE | | histaminic | | | DUKE | | immunomodulator | 50846 | Biologically active substance whose activity affects or plays a role in the functioning of the immune system. | DUKE | | insecticide | 24852 | Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects. | DUKE | | insectifuge | 24852 | Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects. | DUKE | | interleukin-6 inhibitor | 35222 | A substance that diminishes the rate of a chemical reaction. | DUKE | | irritant | | | DUKE | | lipolytic | | | DUKE | | myorelaxant | | | DUKE | | nematicide | 25491 | A substance used to destroy pests of the phylum Nematoda (roundworms). | DUKE | | nitric-oxide-genic | | | DUKE | | ornithine-decarboxylase inhibitor | 23924 | A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. | DUKE | | ozone scavenger | | | DUKE | | peristaltic | | | 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 | | photosensitizer | | | DUKE | | sedative | 35717 | A central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety. | DUKE | | transdermal | | | 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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| lemon |
- Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
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- Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
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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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