Record Information |
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Version | 1.0 |
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Created at | 2020-03-19 00:25:19 UTC |
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Updated at | 2020-11-18 16:34:56 UTC |
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CannabisDB ID | CDB000222 |
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Secondary Accession Numbers | Not Available |
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Cannabis Compound Identification |
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Common Name | Blumenol a |
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Description | Blumenol A, also known as vomifoliol, is formally classified as a cyclic ketone although it is biochemically a terpenoid, as it is biosynthesized via isoprene units. Vomifoliol is structurally related to abscisic acid (ABA) but lacks the 2,4-pentadiene side chain. Vomifoliol is a naturally occurring organic compound found in a number of plants, including cannabis (PMID: 6991645 ) and kidney beans ( Ref:DOI ). Vomifoliol is a fruity tasting compound also found in common grape. It was first isolated from the leaves and stems of Dutch-grown hemp and identified as a cannabis constituent in 1976 (PMID: 6991645 ). In one particular study, Vomifoliol exhibited stomatal closure activity in plant epidermal strips ( Ref:DOI ). |
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Structure | |
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Synonyms | Value | Source |
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(4S)-4-Hydroxy-4-[(1E,3R)-3-hydroxybut-1-enyl]-3,5,5-trimethylcyclohex-2-en-1-one | ChEBI | (6S,9R)-6-Hydroxy-3-oxo-alpha-ionol | ChEBI | Blumenol a | ChEBI | Vomifoliol | ChEBI | (6S,9R)-6-Hydroxy-3-oxo-a-ionol | Generator | (6S,9R)-6-Hydroxy-3-oxo-α-ionol | Generator |
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Chemical Formula | C13H20O3 |
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Average Molecular Weight | 224.3 |
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Monoisotopic Molecular Weight | 224.1412 |
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IUPAC Name | (4S)-4-hydroxy-4-[(1E,3R)-3-hydroxybut-1-en-1-yl]-3,5,5-trimethylcyclohex-2-en-1-one |
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Traditional Name | (6S,9R)-vomifoliol |
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CAS Registry Number | 23526-45-6 |
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SMILES | C[C@@H](O)\C=C\[C@@]1(O)C(C)=CC(=O)CC1(C)C |
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InChI Identifier | InChI=1S/C13H20O3/c1-9-7-11(15)8-12(3,4)13(9,16)6-5-10(2)14/h5-7,10,14,16H,8H2,1-4H3/b6-5+/t10-,13-/m1/s1 |
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InChI Key | KPQMCAKZRXOZLB-KOIHBYQTSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. |
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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 | Sesquiterpenoids |
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Direct Parent | Sesquiterpenoids |
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Alternative Parents | |
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Substituents | - Sesquiterpenoid
- Cyclofarsesane sesquiterpenoid
- Megastigmane sesquiterpenoid
- Ionone derivative
- Cyclohexenone
- Tertiary alcohol
- Ketone
- Secondary alcohol
- Cyclic ketone
- Alcohol
- Hydrocarbon derivative
- Organic oxide
- Organooxygen compound
- Organic oxygen compound
- Carbonyl group
- 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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Not Available | Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | logP | Not Available | Not Available |
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Predicted Properties | [] |
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Spectra |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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Predicted GC-MS | Blumenol a, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Blumenol a, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Blumenol a, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Blumenol a, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Blumenol a, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Blumenol a, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Blumenol a, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0a4i-1290000000-6503dbe714326635d7c5 | 2016-08-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0a4r-5960000000-160023ee9b53b92fd109 | 2016-08-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0a4u-9400000000-effb33726aac710baa8b | 2016-08-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-00di-1390000000-3283e5c97745e2da7575 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-05fr-3390000000-6e989e8d0cd753ed3d08 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0pbi-9710000000-e39dfca2324d645f4627 | 2016-08-03 | View Spectrum |
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NMR | Not Available |
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Pathways |
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Pathways | Not Available |
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Protein Targets |
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Enzymes | Not Available |
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Transporters | Not Available |
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Metal Bindings | Not Available |
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Receptors | Not Available |
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Transcriptional Factors | Not Available |
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Concentrations Data |
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External Links |
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HMDB ID | Not Available |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FoodDB ID | Not Available |
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KNApSAcK ID | C00029834 |
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Chemspider ID | Not Available |
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KEGG Compound ID | C01760 |
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BioCyc ID | --6-HYDROXY-3-OXO-ALPHA-IONOL |
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BiGG ID | Not Available |
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Wikipedia Link | Not Available |
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METLIN ID | Not Available |
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PubChem Compound | 5280462 |
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PDB ID | Not Available |
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ChEBI ID | 49164 |
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References |
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General References | - Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
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