| Record Information |
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| Version | 1.0 |
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| Creation date | 2010-04-08 22:10:20 UTC |
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| Update date | 2019-11-26 03:07:29 UTC |
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| Primary ID | FDB012734 |
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| Secondary Accession Numbers | Not Available |
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| Chemical Information |
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| FooDB Name | Diosgenin |
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| Description | Diosgenin is a member of the class of compounds known as triterpenoids. Triterpenoids are terpene molecules containing six isoprene units. Diosgenin is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Diosgenin can be found in a number of food items such as carrot, wild carrot, yam, and bitter gourd, which makes diosgenin a potential biomarker for the consumption of these food products. Diosgenin, a phytosteroid sapogenin, is the product of hydrolysis by acids, strong bases, or enzymes of saponins, extracted from the tubers of Dioscorea wild yam, such as the Kokoro. The sugar-free (aglycone) product of such hydrolysis, diosgenin is used for the commercial synthesis of cortisone, pregnenolone, progesterone, and other steroid products . |
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| CAS Number | 512-04-9 |
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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 | C27H42O3 |
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| IUPAC name | (1'S,2R,2'S,4'S,5R,7'S,8'R,9'S,12'S,13'R,16'S)-5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosan]-18'-en-16'-ol |
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| InChI Identifier | InChI=1S/C27H42O3/c1-16-7-12-27(29-15-16)17(2)24-23(30-27)14-22-20-6-5-18-13-19(28)8-10-25(18,3)21(20)9-11-26(22,24)4/h5,16-17,19-24,28H,6-15H2,1-4H3 |
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| InChI Key | WQLVFSAGQJTQCK-UHFFFAOYSA-N |
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| Isomeric SMILES | CC1C2C(CC3C4CC=C5CC(O)CCC5(C)C4CCC23C)OC11CCC(C)CO1 |
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| Average Molecular Weight | 414.6206 |
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| Monoisotopic Molecular Weight | 414.31339521 |
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| Classification |
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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
- Spirostane skeleton
- 3-hydroxy-delta-5-steroid
- 3-hydroxysteroid
- Hydroxysteroid
- 3-beta-hydroxy-delta-5-steroid
- 3-beta-hydroxysteroid
- Steroid
- Delta-5-steroid
- Ketal
- Oxane
- Tetrahydrofuran
- Cyclic alcohol
- Secondary alcohol
- Acetal
- Organoheterocyclic compound
- Oxacycle
- Organic oxygen compound
- Organooxygen compound
- Alcohol
- Hydrocarbon derivative
- Aliphatic heteropolycyclic compound
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| Molecular Framework | Aliphatic heteropolycyclic 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 78.21%; H 10.21%; O 11.58% | DFC |
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| Melting Point | Mp 204-207° | DFC |
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| Boiling Point | Not Available | |
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| Experimental Water Solubility | 2e-05 mg/mL at 25 oC | YALKOWSKY,SH & DANNENFELSER,RM (1992) |
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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 | [a]25D -129 (c, 1.4 in CHCl3) | DFC |
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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 | Not Available |
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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 | C08898 |
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| Pubchem Compound ID | 234096 |
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| Pubchem Substance ID | Not Available |
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| ChEBI ID | 495816 |
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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 | HBL90-H:HKK91-O |
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| EAFUS ID | Not Available |
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| Dr. Duke ID | DIOSGENIN |
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| BIGG ID | Not Available |
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| KNApSAcK ID | C00003576 |
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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 | Not Available |
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| SuperScent ID | Not Available |
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| Wikipedia ID | Diosgenin |
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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 | |
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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 | Not Available |
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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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