U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry MIXED
Molecular Formula C30H62
Molecular Weight 422.8144
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SQUALANE

SMILES

CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C

InChI

InChIKey=PRAKJMSDJKAYCZ-UHFFFAOYSA-N
InChI=1S/C30H62/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/h25-30H,9-24H2,1-8H3

HIDE SMILES / InChI

Description
Curator's Comment:: US8980283, US8980288, US8980285; https://www.ncbi.nlm.nih.gov/pubmed/19634915; http://www.fda.gov/cosmetics/registrationprogram/paperregistration/ucm111317.htm; http://www.accessdata.fda.gov/cdrh_docs/pdf7/k073246.pdf

Squalane is an emollient used as cosmetic ingredient. It naturally occurs in small amounts in the lipid layers of skin, and along with its precursor squalene, prevents moisture loss while restoring skin’s suppleness and flexibility. It is soluble in all common cosmetic media, and can be used without limits in all types of formulations being non-toxic and a non-irritant. It is used in skin care products as an active or inactive ingredient and can be used in emulsion composition in vaccines and some drug compositions. Squalane is a hydrogenated squalene - a natural product first extracted from shark liver oil, and later isolated from olive and palm oils. In a pure state, it is a mobile, colorless, odorless and tasteless hydrocarbon oil with good physical and chemical stability. Up to date, anticancer, antioxidant, drug carrier, detoxifier, skin hydrating, and emollient activities of squalane have been reported both in animal models and in vitro environments.

Originator

Curator's Comment:: Early in the 20th century, a highly unsaturated hydrocarbon was independently isolated from shark liver oil by Marcelet, Chapman and Tsujimoto and named as squalene. Around 1950 Sebastien Sabetay at the French company Laserson and Sabetay hydrogenated squalene to form squalane (perhydrosqualene) and beeing commercialized as an important cosmetic ingredient

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Inactive ingredient
HERBALIFE SKIN 7 DAY RESULTS KIT

Approved Use

Helps prevent sunburn. If used as directed with other sun protection measures, decreases the risk of skin cancer and early skin aging caused by the sun.
PubMed

PubMed

TitleDatePubMed
Structure of three new terpenoids, spiciformisins a and b, and monocyclosqualene, isolated from the herbs of Ligularia fischeri var. spiciformis and cytotoxicity.
2002 Dec
Transitions between smooth and complex stick-slip sliding of surfaces.
2003 Aug
Reactor design and kinetics study of 4,4'-dichlorobiphenyl photodecay in surfactant solution by using a photosensitizer and hydrogen source.
2003 May
Remediation of contaminated soil by a solvent/surfactant system.
2003 Oct
Alkanindiges illinoisensis gen. nov., sp. nov., an obligately hydrocarbonoclastic, aerobic squalane-degrading bacterium isolated from oilfield soils.
2003 Sep
Superlubricity: a paradox about confined fluids resolved.
2004 Aug 27
The interaction of monosubstituted benzenes with the stationary liquid in gas liquid chromatography.
2004 Feb
Spectroscopy of the conformational disorder in molecular films: tetracosane and squalane on Pt(111).
2004 Feb 1
Capillary gas chromatography-mass spectrometry of all 93 acyclic octenes and their identification in fluid catalytic cracked gasoline.
2004 Feb 6
Synthesis, characterization and transfection activity of new saturated and unsaturated cationic lipids.
2004 Nov
Entropy-enthalpy compensations in solutions of dual character molecules with polymeric chromatographic liquid phases.
2005 Feb 10
The effects of surface temperature on the gas-liquid interfacial reaction dynamics of O(3P)+squalane.
2005 Jan 8
Intramolecular dynamics of 1,2,3-trifluorobenzene radical anions as studied by OD ESR and quantum-chemical methods.
2005 May 19
Phase behavior of diglycerol fatty acid esters-nonpolar oil systems.
2006 Feb 14
Direct gas-liquid interfacial dynamics: the reaction between O(3P) and a liquid hydrocarbon.
2006 Feb 16
Mechanistic insights into triterpene synthesis from quantum mechanical calculations. Detection of systematic errors in B3LYP cyclization energies.
2006 Feb 7
Nonionic ortho ester surfactants as cleavable emulsifiers.
2006 Jul 1
Microemulsions of triglyceride-based oils: The effect of co-oil and salinity on phase diagrams.
2006 Jul-Aug
Mild TiIII- and Mn/ZrIV-catalytic reductive coupling of allylic halides: efficient synthesis of symmetric terpenes.
2007 Apr 13
The EACN scale for oil classification revisited thanks to fish diagrams.
2007 Aug 1
Wetting and electrical properties of the human hair surface: delipidation observed at the nanoscale.
2007 Feb 1
Theoretical investigation of hyperthermal reactions at the gas-liquid interface: O (3P) and squalane.
2007 Jun 14
Effect of water on foaming properties of diglycerol fatty acid ester-oil systems.
2007 Jun 19
Three-dimensional topographic index applied to the prediction of acyclic C5-C8 alkenes Kováts retention indices on polydimethylsiloxane and squalane columns.
2007 Jun 29
Comparative study of normal and branched alkane monolayer films adsorbed on a solid surface. II. Dynamics.
2007 Mar 14
Comparative study of normal and branched alkane monolayer films adsorbed on a solid surface. I. Structure.
2007 Mar 14
Diversifying the solid state and lyotropic phase behavior of nonionic urea-based surfactants.
2007 Sep 13
Solution-liquid-solid (SLS) growth of silicon nanowires.
2008 Apr 23
Lipid biomarker and phylogenetic analyses to reveal archaeal biodiversity and distribution in hypersaline microbial mat and underlying sediment.
2008 Aug
Squeeze-out of branched alkanes on graphite.
2008 Feb 22
Semi-empirical topological index: development of QSPR/QSRR and optimization for alkylbenzenes.
2008 Jul 15
Exosomes as a tumor immune escape mechanism: possible therapeutic implications.
2008 Jul 22
New contributions to the photophysical model for all-trans-polyenes from ttbP4, a nonphotolabile octatetraene.
2008 Mar 14
Apparent and true enantioselectivity of single- and binary-selector chiral stationary phases in gas chromatography.
2008 Mar 14
Enhanced mucosal and systemic immune response with squalane oil-containing multiple emulsions upon intranasal and oral administration in mice.
2008 May
Hexagonal phase based gel-emulsion (O/H1 gel-emulsion): formation and rheology.
2008 Nov 4
Dynamics of the reaction of O(3P) atoms with alkylthiol self-assembled monolayers.
2009 Apr 23
Immunological mechanisms underlying protection mediated by RTS,S: a review of the available data.
2009 Dec 30
Collisions of DCl with a solution covered with hydrophobic and hydrophilic ions: tetrahexylammonium bromide in glycerol.
2009 Jul 2
Modeling reactive scattering of F(2P) at a liquid squalane interface: a hybrid QM/MM molecular dynamics study.
2009 Jul 2
From protons to OXPHOS supercomplexes and Alzheimer's disease: structure-dynamics-function relationships of energy-transducing membranes.
2009 Jun
Liquid Spreading under Nanoscale Confinement.
2009 Mar 13
Structure of poly(styrene-b-ethylene-alt-propylene) diblock copolymer micelles in squalane.
2009 Oct 22
Anticancer efficacy of squalenoyl gemcitabine nanomedicine on 60 human tumor cell panel and on experimental tumor.
2009 Sep-Oct
Lipid mediators in acne.
2010
Acanthopanax koreanum fruit waste inhibits lipopolysaccharide-induced production of nitric oxide and prostaglandin E2 in RAW 264.7 macrophages.
2010
Comparison of the mobilities of negative and positive ions in nonpolar solutions.
2010 Aug 5
Compositional ripening of particle- and surfactant-stabilised emulsions: a comparison.
2010 Mar 7
Activation energy of the two-proton phototautomerism in 7-azaindole dimer and its medium-dependence.
2010 May 13
First investigation of the microbiology of the deepest layer of ocean crust.
2010 Nov 5
Patents

Sample Use Guides

Use as skin protectant. Apply proper amount to the skin (contains 6g/100 ml Squalane) in combination with immondsia Chinensis (Jojoba) Seed Oil, Argania Spinosa Kernel Oil, Limnanthes Alba (Meadowfoam) Seed Oil.
Route of Administration: Topical
Name Type Language
SQUALANE
EP   II   INCI   MART.   MI   USP-RS   VANDF   WHO-DD  
INCI  
Official Name English
NSC-6851
Code English
SQUALANE [EP]
Common Name English
HEXAMETHYLTETRACOSANE
Systematic Name English
SQUALANE [II]
Common Name English
SQUALANE [EP MONOGRAPH]
Common Name English
SQUALANE [VANDF]
Common Name English
SQUALANE [USP-RS]
Common Name English
SQUALANE [INCI]
Common Name English
SQUALANE [MI]
Common Name English
SQUALANE [MART.]
Common Name English
2,6,10,15,19,23-HEXAMETHYLTETRACOSANE
Systematic Name English
SQUALANE [WHO-DD]
Common Name English
PRIPURE 3759
Brand Name English
Classification Tree Code System Code
EPA PESTICIDE CODE 45503
Created by admin on Fri Jun 25 21:19:59 UTC 2021 , Edited by admin on Fri Jun 25 21:19:59 UTC 2021
Code System Code Type Description
FDA UNII
GW89575KF9
Created by admin on Fri Jun 25 21:19:59 UTC 2021 , Edited by admin on Fri Jun 25 21:19:59 UTC 2021
PRIMARY
USP_CATALOG
1619505
Created by admin on Fri Jun 25 21:19:59 UTC 2021 , Edited by admin on Fri Jun 25 21:19:59 UTC 2021
PRIMARY USP-RS
WIKIPEDIA
SQUALANE
Created by admin on Fri Jun 25 21:19:59 UTC 2021 , Edited by admin on Fri Jun 25 21:19:59 UTC 2021
PRIMARY
ECHA (EC/EINECS)
203-825-6
Created by admin on Fri Jun 25 21:19:59 UTC 2021 , Edited by admin on Fri Jun 25 21:19:59 UTC 2021
PRIMARY
EVMPD
SUB15360MIG
Created by admin on Fri Jun 25 21:19:59 UTC 2021 , Edited by admin on Fri Jun 25 21:19:59 UTC 2021
PRIMARY
ChEMBL
CHEMBL1552157
Created by admin on Fri Jun 25 21:19:59 UTC 2021 , Edited by admin on Fri Jun 25 21:19:59 UTC 2021
PRIMARY
NCI_THESAURUS
C76734
Created by admin on Fri Jun 25 21:19:59 UTC 2021 , Edited by admin on Fri Jun 25 21:19:59 UTC 2021
PRIMARY
PUBCHEM
8089
Created by admin on Fri Jun 25 21:19:59 UTC 2021 , Edited by admin on Fri Jun 25 21:19:59 UTC 2021
PRIMARY
MERCK INDEX
M10165
Created by admin on Fri Jun 25 21:19:59 UTC 2021 , Edited by admin on Fri Jun 25 21:19:59 UTC 2021
PRIMARY Merck Index
EPA CompTox
111-01-3
Created by admin on Fri Jun 25 21:19:59 UTC 2021 , Edited by admin on Fri Jun 25 21:19:59 UTC 2021
PRIMARY
DRUG BANK
DB11420
Created by admin on Fri Jun 25 21:19:59 UTC 2021 , Edited by admin on Fri Jun 25 21:19:59 UTC 2021
PRIMARY
NCI_THESAURUS
C45678
Created by admin on Fri Jun 25 21:19:59 UTC 2021 , Edited by admin on Fri Jun 25 21:19:59 UTC 2021
CONCEPT Industrial Aid
MESH
C019556
Created by admin on Fri Jun 25 21:19:59 UTC 2021 , Edited by admin on Fri Jun 25 21:19:59 UTC 2021
PRIMARY
CAS
111-01-3
Created by admin on Fri Jun 25 21:19:59 UTC 2021 , Edited by admin on Fri Jun 25 21:19:59 UTC 2021
PRIMARY
RXCUI
1363644
Created by admin on Fri Jun 25 21:19:59 UTC 2021 , Edited by admin on Fri Jun 25 21:19:59 UTC 2021
PRIMARY RxNorm