| Record Information |
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| Version | 1.0 |
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| Creation date | 2015-10-09 22:32:47 UTC |
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| Update date | 2017-01-19 02:36:37 UTC |
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| FoodComEx ID | PC000806 |
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| FoodDB Record | FDB013518 |
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| Chemical Information |
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| Name | Uvaol |
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| Description | Constituent of olive oil and Osmanthus fragrans (sweet osmanthus)
Uvaol is a pentacyclic triterpene, found in the non-glyceride fraction of olive pomace oil (Olive pomace oil, also known as "orujo" olive oil, is a blend of refined-pomace oil and virgin olive oil, fit for human consumption). Pentacyclic triterpenes are natural compounds which are widely distributed in plants. These natural products have been demonstrated to possess anti-inflammatory properties. Triterpenoids have been reported to possess antioxidant properties, since they prevent lipid peroxidation and suppress superoxide anion generation. The triterpenes have a history of medicinal use in many Asian countries. Uvaol exhibits both pro- and anti-inflammatory properties depending on chemical structure and dose and may be useful in modulating the immune response; further studies are required to confirm the immunomodulatory behaviour of this triterpenoid, and characterise the mechanisms underlying the biphasic nature of some aspects of the inflammatory response. (PMID: 17292619) |
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| CAS Number | 545-46-0 |
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| Structure | |
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| Synonyms | | Synonym | Source |
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| (3.beta.)-urs-12-ene-3,28-diol | HMDB | | (3beta)-Urs-12-ene-3,28-diol | biospider | | Urs-12-ene-3,28-diol | biospider | | Urs-12-ene-3beta,28-diol | biospider | | Uvaol | db_source |
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| Chemical Formula | C30H50O2 |
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| IUPAC name | 8a-(hydroxymethyl)-4,4,6a,6b,11,12,14b-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-ol |
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| InChI Identifier | InChI=1S/C30H50O2/c1-19-10-15-30(18-31)17-16-28(6)21(25(30)20(19)2)8-9-23-27(5)13-12-24(32)26(3,4)22(27)11-14-29(23,28)7/h8,19-20,22-25,31-32H,9-18H2,1-7H3 |
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| InChI Key | XUARCIYIVXVTAE-UHFFFAOYSA-N |
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| Isomeric SMILES | CC1CCC2(CO)CCC3(C)C(=CCC4C5(C)CCC(O)C(C)(C)C5CCC34C)C2C1C |
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| Average Molecular Weight | 442.7168 |
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| Monoisotopic Molecular Weight | 442.381080844 |
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| Chemical Taxonomy |
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| Description | Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six 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 | Triterpenoids |
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| Direct Parent | Triterpenoids |
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| Alternative Parents | |
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| Substituents | - Triterpenoid
- Cyclic alcohol
- Secondary alcohol
- Organic oxygen compound
- Hydrocarbon derivative
- Primary alcohol
- Organooxygen compound
- Alcohol
- Aliphatic homopolycyclic compound
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| Molecular Framework | Aliphatic homopolycyclic compounds |
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| External Descriptors | Not Available |
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| Physico-Chemical Properties - Experimental |
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| Property | Value | Reference |
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| Experimental logP | Not Available | |
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| Experimental Water Solubility | Not Available | |
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| Melting Point | Mp 232-233° | DFC |
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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 20 mg |
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| Delivery Time | Not Available |
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| Storage Form | solid |
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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 | W2619 |
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| Toronto Research Chemicals | U850180 |
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