创建日期
2005-11-16 15:48:42 UTC
更新日期
2020-09-18 19:23:28 UTC
描述
Squalene is an unsaturated aliphatic hydrocarbon (carotenoid) with six unconjugated double bonds found in human sebum (5%), fish liver oils, yeast lipids, and many vegetable oils (e.g. palm oil, cottonseed oil, rapeseed oil). Squalene is a volatile component of the scent material from Saguinus oedipus (cotton-top tamarin monkey) and Saguinus fuscicollis (saddle-back tamarin monkey) (Hawley's Condensed Chemical Reference). Squalene is a component of adult human sebum that is principally responsible for fixing fingerprints (ChemNetBase). It 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. Squalene is a 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. 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 shark's liver, is lighter than water with a specific gravity of 0.855 (Wikipedia) Squalene is used as a bactericide. It is also an intermediate in the manufacture of pharmaceuticals, rubber chemicals, and colouring materials (Physical Constants of Chemical Substances).
同义词
1:(all-e)-2,6,10,15,19,23-Hexamethyl-2,6,10,14,18,22-tetracosahexaene
2:Spinacene
3:Supraene
4:(e,e,e,e)-Squalene
5:all-trans-Squalene
6:trans-Squalene
7:Squalene
化学名称
(6E,10E,14E,18E)-2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene
代谢物结构字符串
CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C=C(/C)CC\C=C(/C)CCC=C(C)C
inchi标识符
InChI=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+
印记键
YYGNTYWPHWGJRM-AAJYLUCBSA-N
分类学
description: belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.
description:Triterpenoids
kingdom:Organic compounds
super_class:Lipids and lipid-like molecules
class:Prenol lipids
sub_class:Triterpenoids
molecular_framework:Aliphatic acyclic compounds
1:Acyclic olefins
2:Branched unsaturated hydrocarbons
3:Unsaturated aliphatic hydrocarbons
4:Acyclic olefin
5:Aliphatic acyclic compound
6:Branched unsaturated hydrocarbon
7:Hydrocarbon
8:Olefin
9:Triterpenoid
10:Unsaturated aliphatic hydrocarbon
11:Unsaturated hydrocarbon
12:Acyclic triterpenoids
13:Acyclic triterpenoids
14:Liner triterpenes
15:triterpene
本体论
term:Disposition
definition:A concept that describes the origin of a chemical, its location within an organism, or its route of exposure.
parent_id:
level:1
type:parent
term:Route of exposure
definition:A mean by which a chemical agent comes in contact with an organism, either under intended or unintended circumstances.
parent_id:7724
*level:2
type:parent
term:Enteral
definition:Chemical exposure via the alimentary canal (mouth to anus).
parent_id:7743
**level:3
type:parent
term:Ingestion
definition:Chemical exposure facilitated by entry through the mouth.
parent_id:7744
***level:4
type:child
synonym:Digestion
term:Source
definition:Natural or synthetic origin of a chemical.
parent_id:7724
*level:2
type:parent
term:Endogenous
definition:
parent_id:7735
**level:3
type:child
term:Food
definition:
parent_id:7735
**level:3
type:child
term:Biological
definition:A living organism (species or a higher taxonomy rank), in which a chemical can be found.
parent_id:7735
**level:3
type:parent
term:Plant
definition:A living organism belonging to the kingdom plantea. typically, it grows in a permanent site, absorbs water and inorganic substances through its roots, and synthesizes nutrients in its leaves by photosynthesis using the green pigment chlorophyll. examples incude trees, shrubs, herbs, grasses, ferns, and mosses.
parent_id:7736
***level:4
type:child
synonym:Flora
term:Animal
definition:A living organism belonging to the kingdom animalia. it feeds on organic matter, typically having specialized sense organs and nervous system and able to respond rapidly to stimuli.
parent_id:7736
***level:4
type:child
synonym:Fauna
term:Biological location
definition:The physiological origin within an organism, including anatomical compnents, biofluids and excreta.
parent_id:7724
*level:2
type:parent
term:Tissue and substructures
definition:An anatomical organizational level including multiple cells yet not comprising a complete organ .
parent_id:7725
**level:3
type:parent
term:Epidermis
definition:The epithelial portion of the skin (cutis). it consists of the following layers: stratum corneum (horny layer), stratum granulosum (granular layer), stratum spinosum (prickle cell layer), and stratum basale (basal cell layer). (nci).
parent_id:7729
***level:4
type:child
term:Cell and elements
definition:An anatomical organizational level comprising of a single cell (or a fragment in some exceptions). a cell is defined by its type or function. it is the smallest unit of living structure capable of independent existence, composed of a membrane-enclosed mass of protoplasm and containing a nucleus or nucleoid.
parent_id:7725
**level:3
type:parent
term:Extracellular
definition:The space external to the outermost structure of a cell.
parent_id:7732
***level:4
type:child
synonym:Extracellular region
term:Cell
definition:
parent_id:7732
***level:4
type:parent
term:Organ and components
definition:An anatomical organizational level including multiple tissues or substructures, which enables a common biological function.
parent_id:7725
**level:3
type:parent
term:Testicle
definition:Either of the paired male reproductive glands that produce the male germ cells and the male hormones. (nci).
parent_id:7727
***level:4
type:child
synonym:Testes
synonym:Testis
term:Liver
definition:An abdominal organ that has variable lobation which are composed mainly of hepatic lobules. (nci).
parent_id:7727
***level:4
type:child
term:Skin
definition:An organ that constitutes the external surface of the body. it consists of the epidermis, dermis, and skin appendages. (nci).
parent_id:7727
***level:4
type:child
term:Biofluid and excreta
definition:A liquid, semi-solid or solid material originating in the body.
parent_id:7725
**level:3
type:parent
term:Feces
definition:The material discharged from the bowel during defecation. It consists of undigested food, intestinal mucus, epithelial cells, and bacteria.
parent_id:7731
***level:4
type:child
synonym:Fecal
synonym:Stool
synonym:Faecal
synonym:Faeces
term:Blood
definition:A liquid tissue with the primary function of transporting oxygen and carbon dioxide (nci). it supplies the tissues with nutrients, removes waste products, and contains various components of the immune system defending the body against infection.
parent_id:7731
***level:4
type:child
term:Sweat
definition:Secretion produced by a sweat gland.
parent_id:7731
***level:4
type:child
term:Subcellular
definition:An anatomical organizational level including a component within a biological cell .
parent_id:7725
**level:3
type:parent
term:Membrane
definition:
parent_id:7730
***level:4
type:child
term:Endoplasmic reticulum
definition:A network of tubular membranes within the cytoplasm of the cell, occurring either with a smooth surface (smooth endoplasmic reticulum) or studded with ribosomes (rough endoplasmic reticulum), involved in the transport of materials. (Infoplease Dictionary via NCI)
parent_id:7730
***level:4
type:child
synonym:Er
term:Cell membrane
definition:A cellular compartment that separates a cellВ interiorВ from its exterior.
parent_id:7730
***level:4
type:child
synonym:Cellular membrane
term:Cytoplasm
definition:The portion of the cell contained within the plasma membrane but excluding the nucleus.
parent_id:7730
***level:4
type:child
synonym:Cytoplasma
term:Process
definition:Biological or chemical events, or a series thereof, leading to a known function or end-product.
parent_id:
level:1
type:parent
term:Naturally occurring process
definition:Naturally-occurring molecular events or a series thereof, leading to a known function or end-product.
parent_id:7659
*level:2
type:parent
term:Biological process
definition:Biological or chemical events or a series thereof, leading to a known function or end-product within an organism.
parent_id:7660
**level:3
type:parent
term:Biochemical process
definition:A biological process occurring at the subcellular level, involving biochemical reactions.
parent_id:7661
***level:4
type:parent
term:Chemical reaction
definition:A defined chemical event that occurs within or between organism cells.
parent_id:7661
***level:4
type:parent
term:Cellular process
definition:A biological process occurring within a cell or its surroundings.
parent_id:7661
***level:4
type:parent
term:Biochemical pathway
definition:A linked series of chemical reactions that occur in a defined order within or between organism cells, and lead to a known function or end product.
parent_id:7661
***level:4
type:parent
term:Role
definition:The purpose or function assumed by a chemical, either naturally or as intended by humans .
parent_id:
level:1
type:parent
term:Industrial application
definition:The assumed function of a chemical utilized by human.
parent_id:7671
*level:2
type:parent
term:Surfactant
definition:A chemical substance that has the ability to lower the surface tension of water or to reduce the interfacial tension between two immiscible substances. in the cspa consumer product ingredients dictionary, surfactants are classified on the basis of their ionic characteristics, as amphoteric, anionic, cationic, or nonionic; and functions, which are subdivided into the following major groups: surfactant - cleaning agent, surfactant - conditioning agent, surfactant - emulsifying agent, surfactant - foam booster , surfactant hydrotrop , surfactant - solubility agent, surfactant - suspending agent.
parent_id:7678
**level:3
type:child
synonym:Surface-active agent
term:Emulsifier
definition:Substances that promote the formation and stability of a suspension of fine particles of a liquid in another liquid.
parent_id:7678
**level:3
type:child
term:Biological role
definition:The biological function of a chemical. the biological role answers the question how a chemical is involved in molecular processes in an organism. this can include biochemical effects of non-endogenous chemicals, which are also assigned an industrial application such as pharmaceuticals. the biological role is limited to cellular levls, and will not include role at system process level, such as a chemical which has a role in a disease.
parent_id:7671
*level:2
type:parent
term:Membrane stabilizer
definition:A chemical substance that supports the formation and maintenance of a structurally-sound and functioning cell or organelle membrane. Phospholipids form a bilayer and maintain the stability of the membrane structure together with proteins, and other lipids (i.e. cholesterol) which further strengthen it and decrease its permeability.
parent_id:7672
**level:3
type:child
synonym:Membrane stability agent
synonym:Membrane integrity agent
term:Energy source
definition:
parent_id:7672
**level:3
type:child
term:Energy storage
definition:A chemical substance which can be utilized for production of energy in the organism.
parent_id:7672
**level:3
type:child
term:Nutrient
definition:A chamical substance in food, further ingested and utilized by an organism for its well-being, growth and reproduction.
parent_id:7672
**level:3
type:child
实验性质
1:
kind:melting_point
value:-75 °C
source:
预测性质
1:
kind:logp
value:8.64
source:ALOGPS
2:
kind:logs
value:-5.91
source:ALOGPS
3:
kind:solubility
value:5.020E-04 g/L
source:ALOGPS
4:
kind:logp
value:10.42
source:ChemAxon
5:
kind:iupac
value:(6E,10E,14E,18E)-2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene
source:ChemAxon
6:
kind:average_mass
value:410.73
source:ChemAxon
7:
kind:mono_mass
value:410.39125161
source:ChemAxon
8:
kind:smiles
value:CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C=C(/C)CC\C=C(/C)CCC=C(C)C
source:ChemAxon
9:
kind:formula
value:C30H50
source:ChemAxon
10:
kind:inchi
value:InChI=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+
source:ChemAxon
11:
kind:inchikey
value:YYGNTYWPHWGJRM-AAJYLUCBSA-N
source:ChemAxon
12:
kind:polar_surface_area
value:0
source:ChemAxon
13:
kind:refractivity
value:144.62
source:ChemAxon
14:
kind:polarizability
value:56.17
source:ChemAxon
15:
kind:rotatable_bond_count
value:15
source:ChemAxon
16:
kind:acceptor_count
value:0
source:ChemAxon
17:
kind:donor_count
value:0
source:ChemAxon
18:
kind:physiological_charge
value:0
source:ChemAxon
19:
kind:formal_charge
value:0
source:ChemAxon
20:
kind:number_of_rings
value:0
source:ChemAxon
21:
kind:bioavailability
value:No
source:ChemAxon
22:
kind:rule_of_five
value:No
source:ChemAxon
23:
kind:ghose_filter
value:No
source:ChemAxon
24:
kind:veber_rule
value:No
source:ChemAxon
25:
kind:mddr_like_rule
value:No
source:ChemAxon
生物学性质
1:
cellular:(1):Endoplasmic reticulum
cellular:(2):Extracellular
cellular:(3):Membrane
2:
biospecimen:(1):Blood
biospecimen:(2):Feces
biospecimen:(3):Sweat
3:
tissue:(1):Epidermis
tissue:(2):Fibroblasts
tissue:(3):Liver
tissue:(4):Testis
4:
[1]:
name:Alendronate Action Pathway
smpdb_id:SMP00095
kegg_map_id:
[2]:
name:Atorvastatin Action Pathway
smpdb_id:SMP00131
kegg_map_id:
[3]:
name:Cerivastatin Action Pathway
smpdb_id:SMP00111
kegg_map_id:
[4]:
name:CHILD Syndrome
smpdb_id:SMP00387
kegg_map_id:
[5]:
name:Cholesteryl ester storage disease
smpdb_id:SMP00508
kegg_map_id:
[6]:
name:Chondrodysplasia Punctata II, X Linked Dominant (CDPX2)
smpdb_id:SMP00388
kegg_map_id:
[7]:
name:Desmosterolosis
smpdb_id:SMP00386
kegg_map_id:
[8]:
name:Fluvastatin Action Pathway
smpdb_id:SMP00119
kegg_map_id:
[9]:
name:Hyper-IgD syndrome
smpdb_id:SMP00509
kegg_map_id:
[10]:
name:Hypercholesterolemia
smpdb_id:SMP00209
kegg_map_id:
[11]:
name:Ibandronate Action Pathway
smpdb_id:SMP00079
kegg_map_id:
[12]:
name:Lovastatin Action Pathway
smpdb_id:SMP00099
kegg_map_id:
[13]:
name:Lysosomal Acid Lipase Deficiency (Wolman Disease)
smpdb_id:SMP00319
kegg_map_id:
[14]:
name:Mevalonic aciduria
smpdb_id:SMP00510
kegg_map_id:
[15]:
name:Pamidronate Action Pathway
smpdb_id:SMP00117
kegg_map_id:
[16]:
name:Pravastatin Action Pathway
smpdb_id:SMP00089
kegg_map_id:
[17]:
name:Risedronate Action Pathway
smpdb_id:SMP00112
kegg_map_id:
[18]:
name:Rosuvastatin Action Pathway
smpdb_id:SMP00092
kegg_map_id:
[19]:
name:Simvastatin Action Pathway
smpdb_id:SMP00082
kegg_map_id:
[20]:
name:Smith-Lemli-Opitz Syndrome (SLOS)
smpdb_id:SMP00389
kegg_map_id:
[21]:
name:Steroid Biosynthesis
smpdb_id:SMP00023
kegg_map_id:map00100
[22]:
name:Wolman disease
smpdb_id:SMP00511
kegg_map_id:
[23]:
name:Zoledronate Action Pathway
smpdb_id:SMP00107
kegg_map_id:
正常浓度
1:
biospecimen:Blood
concentration_value:2.22 +/- 0.063
concentration_units:uM
subject_age:Adult (>18 years old)
subject_sex:Female
subject_condition:Normal
2:
biospecimen:Blood
concentration_value:1.58 +/- 0.063
concentration_units:uM
subject_age:Adult (>18 years old)
subject_sex:Female
subject_condition:Normal
3:
biospecimen:Feces
concentration_value:
concentration_units:
subject_age:Adult (>18 years old)
subject_sex:Both
subject_condition:Normal
4:
biospecimen:Sweat
concentration_value:
concentration_units:
subject_age:Adult
subject_sex:Both
subject_condition:Normal
异常浓度
1:
biospecimen:Feces
concentration_value:
concentration_units:
patient_age:Adult (>18 years old)
patient_sex:Both
patient_information:Colorectal Cancer
2:
biospecimen:Feces
concentration_value:
concentration_units:
patient_age:Adult (>18 years old)
patient_sex:Both
patient_information:Colorectal Cancer
3:
biospecimen:Feces
concentration_value:
concentration_units:
patient_age:Adult (>18 years old)
patient_sex:Both
patient_information:Colorectal cancer
疾病参考
1:
name:Colorectal cancer
omim_id:114500
[1]:
reference_text:Ishiwata S, Itoh K, Yamaguchi T, Ishida N, Mizugaki M: Comparison of serum and urinary levels of modified nucleoside, 1-methyladenosine, in cancer patients using a monoclonal antibody-based inhibition ELISA. Tohoku J Exp Med. 1995 May;176(1):61-8.
pubmed_id:7482520
[2]:
reference_text:Cheng Y, Xie G, Chen T, Qiu Y, Zou X, Zheng M, Tan B, Feng B, Dong T, He P, Zhao L, Zhao A, Xu LX, Zhang Y, Jia W: Distinct urinary metabolic profile of human colorectal cancer. J Proteome Res. 2012 Feb 3;11(2):1354-63. doi: 10.1021/pr201001a. Epub 2011 Dec 28.
pubmed_id:22148915
[3]:
reference_text:Monleon D, Morales JM, Barrasa A, Lopez JA, Vazquez C, Celda B: Metabolite profiling of fecal water extracts from human colorectal cancer. NMR Biomed. 2009 Apr;22(3):342-8. doi: 10.1002/nbm.1345.
pubmed_id:19006102
[4]:
reference_text:Weir TL, Manter DK, Sheflin AM, Barnett BA, Heuberger AL, Ryan EP: Stool microbiome and metabolome differences between colorectal cancer patients and healthy adults. PLoS One. 2013 Aug 6;8(8):e70803. doi: 10.1371/journal.pone.0070803. Print 2013.
pubmed_id:23940645
[5]:
reference_text:Phua LC, Chue XP, Koh PK, Cheah PY, Ho HK, Chan EC: Non-invasive fecal metabonomic detection of colorectal cancer. Cancer Biol Ther. 2014 Apr;15(4):389-97. doi: 10.4161/cbt.27625. Epub 2014 Jan 14.
pubmed_id:24424155
[6]:
reference_text:Ritchie SA, Ahiahonu PW, Jayasinghe D, Heath D, Liu J, Lu Y, Jin W, Kavianpour A, Yamazaki Y, Khan AM, Hossain M, Su-Myat KK, Wood PL, Krenitsky K, Takemasa I, Miyake M, Sekimoto M, Monden M, Matsubara H, Nomura F, Goodenowe DB: Reduced levels of hydroxylated, polyunsaturated ultra long-chain fatty acids in the serum of colorectal cancer patients: implications for early screening and detection. BMC Med. 2010 Feb 15;8:13. doi: 10.1186/1741-7015-8-13.
pubmed_id:20156336
[7]:
reference_text:Qiu Y, Cai G, Su M, Chen T, Zheng X, Xu Y, Ni Y, Zhao A, Xu LX, Cai S, Jia W: Serum metabolite profiling of human colorectal cancer using GC-TOFMS and UPLC-QTOFMS. J Proteome Res. 2009 Oct;8(10):4844-50. doi: 10.1021/pr9004162.
pubmed_id:19678709
[8]:
reference_text:Ni Y, Xie G, Jia W: Metabonomics of human colorectal cancer: new approaches for early diagnosis and biomarker discovery. J Proteome Res. 2014 Sep 5;13(9):3857-70. doi: 10.1021/pr500443c. Epub 2014 Aug 14.
pubmed_id:25105552
[9]:
reference_text:Ikeda A, Nishiumi S, Shinohara M, Yoshie T, Hatano N, Okuno T, Bamba T, Fukusaki E, Takenawa T, Azuma T, Yoshida M: Serum metabolomics as a novel diagnostic approach for gastrointestinal cancer. Biomed Chromatogr. 2012 May;26(5):548-58. doi: 10.1002/bmc.1671. Epub 2011 Jul 20.
pubmed_id:21773981
[10]:
reference_text:Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18.
pubmed_id:25037050
[11]:
reference_text:Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016.
pubmed_id:27015276
[12]:
reference_text:Lin Y, Ma C, Liu C, Wang Z, Yang J, Liu X, Shen Z, Wu R: NMR-based fecal metabolomics fingerprinting as predictors of earlier diagnosis in patients with colorectal cancer. Oncotarget. 2016 May 17;7(20):29454-64. doi: 10.18632/oncotarget.8762.
pubmed_id:27107423
[13]:
reference_text:Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016.
pubmed_id:27275383
[14]:
reference_text:Wang X, Wang J, Rao B, Deng L: Gut flora profiling and fecal metabolite composition of colorectal cancer patients and healthy individuals. Exp Ther Med. 2017 Jun;13(6):2848-2854. doi: 10.3892/etm.2017.4367. Epub 2017 Apr 20.
pubmed_id:28587349
[15]:
reference_text:Silke Matysik, Caroline Ivanne Le Roy, Gerhard Liebisch, Sandrine Paule Claus. Metabolomics of fecal samples: A practical consideration. Trends in Food Science & Technology. Vol. 57, Part B, Nov. 2016, p.244-255: http://www.sciencedirect.com/science/article/pii/S0924224416301984
综合参考
Peng, Wanxi; Li, Kaifu. Method of preparation of squalene. Faming Zhuanli Shenqing Gongkai Shuomingshu (2006), 9pp.
一般参考
1:
protein_accession:HMDBP00153
name:Squalene monooxygenase
uniprot_id:Q14534
gene_name:SQLE
protein_type:Unknown
2:
protein_accession:HMDBP00260
name:Squalene synthase
uniprot_id:P37268
gene_name:FDFT1
protein_type:Unknown
3:
protein_accession:HMDBP00886
name:Serine palmitoyltransferase 1
uniprot_id:O15269
gene_name:SPTLC1
protein_type:Enzyme
4:
protein_accession:HMDBP07363
name:Putative uncharacterized protein DKFZp686B0215
uniprot_id:Q5HYI4
gene_name:DKFZp686B0215
protein_type:Enzyme
5:
protein_accession:HMDBP10799
name:SEC14-like protein 3
uniprot_id:Q9UDX4
gene_name:SEC14L3
protein_type:Unknown
6:
protein_accession:HMDBP10800
name:SEC14-like protein 4
uniprot_id:Q9UDX3
gene_name:SEC14L4
protein_type:Unknown
蛋白质结合
1:
reference_text: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_id:6444323
2:
reference_text:Grimes DS, Hindle E, Dyer T: Sunlight, cholesterol and coronary heart disease. QJM. 1996 Aug;89(8):579-89.
pubmed_id:8935479
3:
reference_text: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_id:10998465
4:
reference_text: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_id:1568728
5:
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