Squalene
Squalene is a natural raw material found in human sebum (5%) and in shark-liver oil. An unsaturated aliphatic hydrocarbon (carotenoid) with six unconjugated double bonds. (Hawleys Condensed Chemical Reference) Biological Source: Found in fish liver oils, yeast lipids and many vegetable oils, e.g. palm oil, cottonseed oil, rapeseed oil. Volatile component of scent material from Saguinus oedipus (cotton-top tamarin monkey) and Saguinus fuscicollis (saddle-back tamarin monkey). Component of adlit human sebum principally responsible for the fixing of fingerprints (ChemNetBase) Squalene is a natural organic compound originally obtained for commercial purposes primarily from shark liver oil, though there are botanical sources as well, including rice bran, wheat germ, and olives. All higher organisms produce squalene, including humans. It is a hydrocarbon and a triterpene. — Wikipedia; Squalene is the biochemical precursor to the whole family of steroids. Oxidation of one of the terminal double bonds of squalene yields 2,3-squalene oxide which undergoes enzyme-catalyzed cyclization to afford lanosterol, which is then elaborated into cholesterol and other steroids. — Wikipedia; Squalene is a low density compound often stored in the bodies of cartilaginous fishes such as sharks, which lack a swim bladder and must therefore reduce their body density with fats and oils. Squalene, which is stored mainly in the sharks liver, is lighter than water with a specific gravity of 0.855. — Wikipedia Uses: Bactericide. Intermediate in the manufacture of pharmaceuticals, rubber chemicals and coloring materials (Physical Constants of Chemical Substances).
Structure for HMDB00256 (Squalene)
C30H50
410.718
410.3912516
(6Z,10E,14E,18E)-2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene
(6Z,10E,14E,18E)-2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene
111-02-4
YYGNTYWPHWGJRM-FLHYQJCXSA-N
Not classified
Detected and Quantified
Liquid
LC-MS/MS Spectrum – Quattro_QQQ 10V, Positive (Annotated)splash10-047r-1944600000-5faa7a5eb4804dfad261View in MoNA
LC-MS/MS Spectrum – Quattro_QQQ 25V, Positive (Annotated)splash10-000i-4867900000-dcd3ba4f6ee550dc565bView in MoNA
LC-MS/MS Spectrum – Quattro_QQQ 40V, Positive (Annotated)splash10-000i-2944400000-8be7743f6b07ba138c24View in MoNA
1H NMR SpectrumNot Available
[1H,13C] 2D NMR SpectrumNot Available
Normal
Not Available
None
None
Not Available
Not Available
Not Available
Not Available
FDB015781
C00003755
10148626
C00751
SQUALENE
35878
Squalene
HMDB00256
HMDB00256
197
11975273
Not Available
15440
Product: S1p receptor agonist 1
- 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. [PubMed:6444323 ]
- Grimes DS, Hindle E, Dyer T: Sunlight, cholesterol and coronary heart disease. QJM. 1996 Aug;89(8):579-89. [PubMed:8935479 ]
- 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. [PubMed:10998465 ]
- 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. [PubMed:1568728 ]
- 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. [PubMed:9125314 ]
- 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. [PubMed:10758959 ]
- Rajaratnam RA, Gylling H, Miettinen TA: Serum squalene in postmenopausal women without and with coronary artery disease. Atherosclerosis. 1999 Sep;146(1):61-4. [PubMed:10487487 ]
- 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. [PubMed:10594744 ]
- Relas H, Gylling H, Miettinen TA: Effect of stanol ester on postabsorptive squalene and retinyl palmitate. Metabolism. 2000 Apr;49(4):473-8. [PubMed:10778871 ]
- Gylling H, Vuoristo M, Farkkila M, Miettinen TA: The metabolism of cholestanol in primary biliary cirrhosis. J Hepatol. 1996 Apr;24(4):444-51. [PubMed:8738731 ]
- 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. [PubMed:11424225 ]
- Nosaka Y, Yamanishi Y, Hirayama C: Biliary squalene levels in hepatobiliary disease. Gastroenterol Jpn. 1985 Aug;20(4):338-43. [PubMed:4054510 ]
- 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. [PubMed:7742356 ]
Enzymes
- General function:
- Involved in oxidoreductase activity
- Specific function:
- Catalyzes the first oxygenation step in sterol biosynthesis and is suggested to be one of the rate-limiting enzymes in this pathway.
- Gene Name:
- SQLE
- Uniprot ID:
- Q14534
- Molecular weight:
- 63922.505
Reactions
- General function:
- Involved in transferase activity
- Specific function:
- Not Available
- Gene Name:
- FDFT1
- Uniprot ID:
- P37268
- Molecular weight:
- 48114.87
Reactions
- General function:
- Involved in transferase activity, transferring nitrogenous groups
- Specific function:
- Serine palmitoyltransferase (SPT). The heterodimer formed with SPTLC2 or SPTLC3 constitutes the catalytic core. The composition of the serine palmitoyltransferase (SPT) complex determines the substrate preference. The SPTLC1-SPTLC2-SPTSSA complex shows a strong preference for C16-CoA substrate, while the SPTLC1-SPTLC3-SPTSSA isozyme uses both C14-CoA and C16-CoA as substrates, with a slight preference for C14-CoA. The SPTLC1-SPTLC2-SPTSSB complex shows a strong preference for C18-CoA substrate, while the SPTLC1-SPTLC3-SPTSSB isozyme displays an ability to use a broader range of acyl-CoAs, without apparent preference.
- Gene Name:
- SPTLC1
- Uniprot ID:
- O15269
- Molecular weight:
- 52743.41
- General function:
- Involved in oxidoreductase activity
- Specific function:
- Not Available
- Gene Name:
- DKFZp686B0215
- Uniprot ID:
- Q5HYI4
- Molecular weight:
- 63793.4
- General function:
- Involved in transporter activity
- Specific function:
- Probable hydrophobic ligand-binding protein; may play a role in the transport of hydrophobic ligands like tocopherol, squalene and phospholipids
- Gene Name:
- SEC14L3
- Uniprot ID:
- Q9UDX4
- Molecular weight:
- 46047.8
- General function:
- Involved in transporter activity
- Specific function:
- Probable hydrophobic ligand-binding protein; may play a role in the transport of hydrophobic ligands like tocopherol, squalene and phospholipids
- Gene Name:
- SEC14L4
- Uniprot ID:
- Q9UDX3
- Molecular weight:
- 46643.4