Squalene (CHEM030484)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 01:55:28 UTC
Update Date2016-11-09 01:19:05 UTC
Accession NumberCHEM030484
Identification
Common NameSqualene
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(all-e)-2,6,10,15,19,23-Hexamethyl-2,6,10,14,18,22-tetracosahexaeneHMDB
(e,e,e,e)-SqualeneHMDB
2,6,10,15,19,23-Hexamethyl-2,6,10,14,18,22-tetracosahexaeneHMDB
all-trans-SqualeneHMDB
nikko Squalane exHMDB
SpinacenHMDB
SpinaceneHMDB
SqualenHMDB
trans-SqualeneHMDB
Chemical FormulaC30H50
Average Molecular Mass410.718 g/mol
Monoisotopic Mass410.391 g/mol
CAS Registry Number7683-64-9
IUPAC Name(6Z,10E,14E,18E)-2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene
Traditional Name(6Z,10E,14E,18E)-2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene
SMILESCC(C)=CCC\C(C)=C/CC\C(C)=C\CC\C=C(/C)CC\C=C(/C)CCC=C(C)C
InChI IdentifierInChI=1S/C30H50/c1-25(2)15-11-19-29(7)23-13-21-27(5)17-9-10-18-28(6)22-14-24-30(8)20-12-16-26(3)4/h15-18,23-24H,9-14,19-22H2,1-8H3/b27-17+,28-18+,29-23-,30-24+
InChI KeyYYGNTYWPHWGJRM-FLHYQJCXSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTriterpenoids
Direct ParentTriterpenoids
Alternative Parents
Substituents
  • Triterpenoid
  • Branched unsaturated hydrocarbon
  • Unsaturated aliphatic hydrocarbon
  • Unsaturated hydrocarbon
  • Olefin
  • Acyclic olefin
  • Hydrocarbon
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0005 g/LALOGPS
logP8.64ALOGPS
logP10.42ChemAxon
logS-5.9ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity144.62 m³·mol⁻¹ChemAxon
Polarizability55.9 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05y1-4879000000-643c1d087f1a2f3e2e16Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-047r-1944600000-5faa7a5eb4804dfad261Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000i-4867900000-dcd3ba4f6ee550dc565bSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-000i-2944400000-8be7743f6b07ba138c24Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0323900000-5bedc30817d5c5d01efbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0cdl-4984100000-300a277b16ec703823d5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0aou-7596000000-05f1c221b7c0392d38d0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000900000-b358bb76b170bbf30138Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0000900000-263e0536e44752c47006Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-1879100000-92ff711655668bba23d8Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0000256
FooDB IDFDB015781
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkSqualene
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID11975273
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Peng, Wanxi; Li, Kaifu. Method of preparation of squalene. Faming Zhuanli Shenqing Gongkai Shuomingshu (2006), 9pp.
2. Peng, Wanxi; Li, Kaifu. Method of preparation of squalene. Faming Zhuanli Shenqing Gongkai Shuomingshu (2006), 9pp.
3. Strauss JS, Stranieri AM, Farrell LN, Downing DT: The effect of marked inhibition of sebum production with 13cis-retinoic acid on skin surface lipid composition. J Invest Dermatol. 1980 Feb;74(2):66-7.
4. Grimes DS, Hindle E, Dyer T: Sunlight, cholesterol and coronary heart disease. QJM. 1996 Aug;89(8):579-89.
5. Relas H, Gylling H, Miettinen TA: Dietary squalene increases cholesterol synthesis measured with serum non-cholesterol sterols after a single oral dose in humans. Atherosclerosis. 2000 Oct;152(2):377-83.
6. Nikkila K, Hockerstedt K, Miettinen TA: Serum and hepatic cholestanol, squalene and noncholesterol sterols in man: a study on liver transplantation. Hepatology. 1992 May;15(5):863-70.
7. Gylling H, Relas H, Miettinen HE, Radhakrishnan R, Miettinen TA: Delayed postprandial retinyl palmitate and squalene removal in a patient heterozygous for apolipoprotein A-IFIN mutation (Leu 159-->Arg) and low HDL cholesterol level without coronary artery disease. Atherosclerosis. 1996 Dec 20;127(2):239-43.
8. Rajaratnam RA, Gylling H, Miettinen TA: Independent association of serum squalene and noncholesterol sterols with coronary artery disease in postmenopausal women. J Am Coll Cardiol. 2000 Apr;35(5):1185-91.
9. Rajaratnam RA, Gylling H, Miettinen TA: Serum squalene in postmenopausal women without and with coronary artery disease. Atherosclerosis. 1999 Sep;146(1):61-4.
10. Thiele JJ, Weber SU, Packer L: Sebaceous gland secretion is a major physiologic route of vitamin E delivery to skin. J Invest Dermatol. 1999 Dec;113(6):1006-10.
11. Relas H, Gylling H, Miettinen TA: Effect of stanol ester on postabsorptive squalene and retinyl palmitate. Metabolism. 2000 Apr;49(4):473-8.
12. Gylling H, Vuoristo M, Farkkila M, Miettinen TA: The metabolism of cholestanol in primary biliary cirrhosis. J Hepatol. 1996 Apr;24(4):444-51.
13. Chiba K, Yoshizawa K, Makino I, Kawakami K, Onoue M: Changes in the levels of glutathione after cellular and cutaneous damage induced by squalene monohydroperoxide. J Biochem Mol Toxicol. 2001;15(3):150-8.
14. Nosaka Y, Yamanishi Y, Hirayama C: Biliary squalene levels in hepatobiliary disease. Gastroenterol Jpn. 1985 Aug;20(4):338-43.
15. Kohno Y, Egawa Y, Itoh S, Nagaoka S, Takahashi M, Mukai K: Kinetic study of quenching reaction of singlet oxygen and scavenging reaction of free radical by squalene in n-butanol. Biochim Biophys Acta. 1995 Apr 28;1256(1):52-6.