| Record Information |
|---|
| Version | 1.0 |
|---|
| Created at | 2020-03-19 00:30:42 UTC |
|---|
| Updated at | 2020-11-18 16:35:04 UTC |
|---|
| CannabisDB ID | CDB000319 |
|---|
| Secondary Accession Numbers | Not Available |
|---|
| Cannabis Compound Identification |
|---|
| Common Name | dihydrovomifoliol |
|---|
| Description | Dihydrovomifoliol, also known as 4,5-dihydrovomifoliol, belongs to the class of organic compounds known as sesquiterpenoids. While it is chemically classified as a cyclic alcohol it is biochemically a sesquiterpenoid as it is synthesized via multiple isoprene units. Sesquiterpenoids are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA), in the cytosol. However, recent studies have found evidence of pathway crosstalk with the methyl-erythritol-phosphate (MEP) pathway in the cytosol. Farnesyl diphosphate (FPP) is a key intermediate in the biosynthesis of cyclic sesquiterpenes. FPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. There are several isomers of dihydrovomifoliol, including 4,5-Dihydrovomifoliol, 1,8-Dihydrovomifoliol and 7,8-Dihydrovomifoliol. 4,5-Dihydrovomifoliol appears to be the more common isomer in nature. 4,5-Dihydrovomifoliol is a neutral, hydrophobic molecule that is insoluble in water. It has been identified as an aroma constituent in nectarines (PMID: 14518956 ). It was first isolated from the leaves and stems of Dutch-grown hemp and identified as a cannabis constituent in 1976 (PMID: 6991645 ). |
|---|
| Structure | |
|---|
| Synonyms | Not Available |
|---|
| Chemical Formula | C13H22O3 |
|---|
| Average Molecular Weight | 226.32 |
|---|
| Monoisotopic Molecular Weight | 226.1569 |
|---|
| IUPAC Name | (4S,5R)-4-hydroxy-4-[(1E,3R)-3-hydroxybut-1-en-1-yl]-3,3,5-trimethylcyclohexan-1-one |
|---|
| Traditional Name | (4S,5R)-4-hydroxy-4-[(1E,3R)-3-hydroxybut-1-en-1-yl]-3,3,5-trimethylcyclohexan-1-one |
|---|
| CAS Registry Number | Not Available |
|---|
| SMILES | C[C@@H](O)\C=C\[C@@]1(O)[C@H](C)CC(=O)CC1(C)C |
|---|
| InChI Identifier | InChI=1S/C13H22O3/c1-9-7-11(15)8-12(3,4)13(9,16)6-5-10(2)14/h5-6,9-10,14,16H,7-8H2,1-4H3/b6-5+/t9-,10-,13-/m1/s1 |
|---|
| InChI Key | IHDJYDVWNNFPHR-CHESLIBASA-N |
|---|
| Chemical Taxonomy |
|---|
| Description | Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. |
|---|
| Kingdom | Organic compounds |
|---|
| Super Class | Lipids and lipid-like molecules |
|---|
| Class | Prenol lipids |
|---|
| Sub Class | Sesquiterpenoids |
|---|
| Direct Parent | Sesquiterpenoids |
|---|
| Alternative Parents | |
|---|
| Substituents | - Sesquiterpenoid
- Megastigmane sesquiterpenoid
- Cyclofarsesane sesquiterpenoid
- Ionone derivative
- Cyclic alcohol
- Tertiary alcohol
- Ketone
- Secondary alcohol
- Cyclic ketone
- Organooxygen compound
- Alcohol
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Carbonyl group
- Aliphatic homomonocyclic compound
|
|---|
| Molecular Framework | Aliphatic homomonocyclic compounds |
|---|
| External Descriptors | Not Available |
|---|
| Ontology |
|---|
|
Not Available | | Physical Properties |
|---|
| State | Solid |
|---|
| Experimental Properties | | Property | Value | Reference |
|---|
| Melting Point | Not Available | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | Not Available | Not Available | | logP | Not Available | Not Available |
|
|---|
| Predicted Properties | [] |
|---|
