| Common Name |
Campestanol
| Description |
Campestanol is plant stanol. It can decrease the circliating LDL-cholesterol level by reducing intestinal cholesterol absorption. (PMID 8143759 ).
| Structure |
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
| Synonyms |
| Value |
Source |
(24R)-5a-Ergostan-3b-olHMDB
24b-EthylcholestanolHMDB
24b-MethylcholestanolHMDB
5a-DihydrocampesterolHMDB
ChalinastanolHMDB
dihydro-NeospongosterolHMDB
DihydrocampesterinHMDB
| Chemical Formlia |
C28H50O
| Average Molecliar Weight |
402.696
| Monoisotopic Molecliar Weight |
402.386166222
| IUPAC Name |
(1S,2S,10R,11S,14R,15R)-14-[(2R,5R)-5,6-dimethylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-ol
| Traditional Name |
(1S,2S,10R,11S,14R,15R)-14-[(2R,5R)-5,6-dimethylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-ol
| CAS Registry Number |
474-60-2
| SMILES |
[H][C@@]12CC[C@H]([C@H](C)CC[C@@H](C)C(C)C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2CC(O)CC[C@]12C
| InChI Identifier |
InChI=1S/C28H50O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h18-26,29H,7-17H2,1-6H3/t19-,20-,21?,22?,23+,24-,25+,26+,27+,28-/m1/s1
| InChI Key |
ARYTXMNEANMLMU-XKPVSPJHSA-N
| Chemical Taxonomy |
| Classification |
Not classified
| Ontology |
| Status |
Detected and Quantified
| Origin |
Endogenous
Food
| Biofunction |
Cell signaling
Fuel and energy storage
Fuel or energy source
Hormones, Membrane component
Membrane integrity/stability
| Application |
Nutrients
Stabilizers
Surfactants and Emlisifiers
| Cellliar locations |
Extracellliar
Membrane (predicted from logP)
| Physical Properties |
| State |
Solid
| Experimental Properties |
| Property |
Value |
Reference |
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
| Predicted Properties |
| Property |
Value |
Source |
Water Solubility1.31e-05 mg/mLALOGPS
logP6.86ALOGPS
logP7.81ChemAxon
logS-7.5ALOGPS
pKa (Strongest Acidic)18.3ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity124.32 m3·mol-1ChemAxon
Polarizability52.93 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
Not Available
| Biological Properties |
| Cellliar Locations |
Extracellliar
Membrane (predicted from logP)
| Biofluid Locations |
Blood
| Tissue Location |
Not Available
| Pathways |
Not Available
| Normal Concentrations |
| Biofluid |
Status |
Age |
Condition |
Reference |
Details |
BloodDetected and Quantified2.5 +/- 2.5 uMAdlit (>18 years old)BothNormal
12679174
details
|
| Abnormal Concentrations |
|
| Biofluid |
Status |
Age |
Condition |
Reference |
Details |
BloodDetected and Quantified96.9 +/- 4.9 uMAdlit (>18 years old)BothPhytosterolemia
7595097
details
| Associated Disorders and Diseases |
| Disease References |
| Sitosterolemia |
- Lutjohann D, Bjorkhem I, Beil UF, von Bergmann K: Sterol absorption and sterol balance in phytosterolemia evaluated by deuterium-labeled sterols: effect of sitostanol treatment. J Lipid Res. 1995 Aug;36(8):1763-73. [PubMed:7595097 ]
| Associated OMIM IDs |
210250 (Sitosterolemia)
| External Links |
| DrugBank ID |
Not Available
| DrugBank Metabolite ID |
Not Available
| Phenol Explorer Compound ID |
Not Available
| Phenol Explorer Metabolite ID |
Not Available
| FoodDB ID |
FDB001925
| KNApSAcK ID |
C00007516
| Chemspider ID |
17215967
| KEGG Compound ID |
Not Available
| BioCyc ID |
Not Available
| BiGG ID |
Not Available
| Wikipedia Link |
Not Available
| NuGOwiki Link |
HMDB00534
| Metagene Link |
HMDB00534
| METLIN ID |
5519
| PubChem Compound |
22833530
| PDB ID |
Not Available
| ChEBI ID |
Not Available
Product: Xanthohumol
References |
| Synthesis Reference |
Kircher, Henry W.; Rosenstein, Fumiko U. Purification of campesterol and preparation of 7-dehydrocampesterol, 7-campestenol, and campestanol. Lipids (1974), 9(5), 333-7. |
| Material Safety Data Sheet (MSDS) |
Not Available |
| General References |
- Shoemaker JD, Elliott WH: Automated screening of urine samples for carbohydrates, organic and amino acids after treatment with urease. J Chromatogr. 1991 Jan 2;562(1-2):125-38. [PubMed:2026685 ]
- Hoffmann GF, Seppel CK, Holmes B, Mitchell L, Christen HJ, Hanefeld F, Rating D, Nyhan WL: Quantitative organic acid analysis in cerebrospinal fluid and plasma: reference values in a pediatric population. J Chromatogr. 1993 Jul 23;617(1):1-10. [PubMed:8376520 ]
- Phillips KM, Ruggio DM, Bailey JA: Precise quantitative determination of phytosterols, stanols, and cholesterol metabolites in human serum by capillary gas-liquid chromatography. J Chromatogr B Biomed Sci Appl. 1999 Sep 10;732(1):17-29. [PubMed:10517218 ]
- Heinemann T, Axtmann G, von Bergmann K: Comparison of intestinal absorption of cholesterol with different plant sterols in man. Eur J Clin Invest. 1993 Dec;23(12):827-31. [PubMed:8143759 ]
- Plat J, Mensink RP: Effects of plant sterols and stanols on lipid metabolism and cardiovascular risk. Nutr Metab Cardiovasc Dis. 2001 Feb;11(1):31-40. [PubMed:11383323 ]
|
PMID: 18045913