Squalene

Base Information

• Chemical Name: Squalene
• CAS No.: 111-02-4
• Deprecated CAS: 94016-35-0,21245-10-3
• Molecular Formula: C30H50
• Molecular Weight: 410.727
• Hs Code.: 29012980
• European Community (EC) Number: 203-826-1
• NSC Number: 93748
• UNII: 7QWM220FJH
• DSSTox Substance ID: DTXSID0026044
• Nikkaji Number: J5.103I,J8.960E
• Wikipedia: Squalene
• Wikidata: Q407560
• NCI Thesaurus Code: C77219
• RXCUI: 10014
• ChEMBL ID: CHEMBL458402
• Mol file: 111-02-4.mol

Synonyms:Squalene

Chemical Property of Squalene

Chemical Property:

• Appearance/Colour: Clear, slightly yellow liquid with a faint odor.
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: -75 ºC
• Refractive Index: n20/D 1.494(lit.)
• Boiling Point: 285 ºC (25 mmHg)
• Flash Point: 254.1°C
• PSA: 0.00000
• Density: 0.858
• LogP: 10.60500
• Storage Temp.: 2-8°C
• Water Solubility.: <0.1 g/100 mL at 19℃
• XLogP3: 11.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 15
• Exact Mass: 410.391251595
• Heavy Atom Count: 30
• Complexity: 578

Purity/Quality:

99%, ^*data from raw suppliers

Squalene ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Uses -> Lubricants
• Canonical SMILES: CC(=CCCC(=CCCC(=CCCC=C(C)CCC=C(C)CCC=C(C)C)C)C)C
• Isomeric SMILES: CC(=CCC/C(=C/CC/C(=C/CC/C=C(/CC/C=C(/CCC=C(C)C)\C)\C)/C)/C)C
• Recent ClinicalTrials: A Phase I Comparative Blinded Trial of Several HIV-1 Derived Immunogens in Infected Individuals With >= 500 CD4 Cells/mm3
• Uses: Squalene is a natural triterpene that plays an important role in the synthesis of cholesterol, steroid hormones, and vitamin D in the human body. Squalene is commonly used as a biochemical precursor i n the preparation of steroids. Squalene is also a natural moisturizer with low acute toxicity and is not significant human skin irritants or sensitizers. cosmetic and pharmaceutical excipient Bactericide; intermediate in manufacture of pharmaceuticals, organic coloring materials, rubber chemicals, aromatics and surface active agents.

Technology Process of Squalene

There total 71 articles about Squalene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 88.7%

C36H54O2S → 2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene (111-02-4)

Guidance literature:

With bis(diphenylphosphino)propanepalladium(II) dichloride; lithium triethylborohydride; In tetrahydrofuran; at -78 - 20 ℃; for 50h;

Reference yield: 78.0%

Farnesol (106-28-5) → 2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene (111-02-4) + (6E,10E)-2,6,10-trimethyldodeca-2,6,10-triene (3899-18-1) + (E)-3,7,11-trimethyldodeca-1,6,10-triene (66633-32-7)

Guidance literature:

With bis(cyclopentadienyl)titanium dichloride; manganese; In tetrahydrofuran; for 2h; Solvent; regioselective reaction; Inert atmosphere; Reflux;

DOI:10.1039/c4ob02290d

Reference yield: 77.0%

[(6E,10E,14E,18E)-13-(1-ethoxyethoxy)-2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaen-12-yl]sulfonylbenzene (1299297-72-5) → 2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene (111-02-4)

Guidance literature:

With (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride; lithium triethylborohydride; In tetrahydrofuran; 1,4-dioxane; at 20 - 70 ℃; for 10h; Inert atmosphere;

DOI:10.1021/ol200779y

upstream raw materials:

1,4-dibromo-butane

pseudo-ionone

farnesyl bromide

diethyl ether

Downstream raw materials:

(6E,10E,18E)-trans-14,15-epoxy-2,6,10,15,19,23-hexamethyltetracosa-2,6,10,18,22-pentaene

(6E,10E,14E)-trans-18,19-epoxy-2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,22-pentaene

2,3-Oxidosqualene

2,3,22,23-Dioxidosqualene

Refernces

• 1、 Fukuda, Yoriyuki,Watanabe, Takashi,Hoshino, Tsutomu. "Mutated variants of squalene-hopene cyclase: Enzymatic syntheses of triterpenes bearing oxygen-bridged monocycles and a new 6,6,6,6,6-fusded pentacyclic scaffold, named neogammacerane, from 2,3-oxidosqualene". . p. 6987 - 7000. Retrieved 2018.
• 2、 Hoshino, Tsutomu,Sakai, Yoshiyuki. "Enzymic products of the 2,3-oxidosqualene analog having an ethyl residue at 10-position. First trapping of the trimethylcyclohexanone ring by lanosterol synthase". . p. 7319 - 7323. Retrieved 2001.
• 3、 Caspi et al.. "". . p. 3563. Retrieved 1968.
• 4、 Bhalerao,U.T.,Rapoport,H.. "-". . p. 5311 - 5313. Retrieved 1971.
• 5、 Barrero, Alejandro F.,Herrador, M. Mar,Del Moral, Jose F. Quilez,Arteaga, Pilar,Arteaga, Jesus F.,Piedra, Maria,Sanchez, Elena M.. "Reductive coupling of terpenic allylic halides catalyzed by Cp 2TiCl: A short and efficient asymmetric synthesis of onocerane triterpenes". . p. 2301 - 2304. Retrieved 2005.
• 6、 Axelrod,E.H. et al.. "-". . p. 2139 - 2141. Retrieved 1970.
• 7、 Karrer. "-". . p. 130. Retrieved 1953.
• 8、 -. "SYNTHESIS OF E,E-FARNESOL, FARNESYL ACETATE AND SQUALENE FROM FARNESENE VIA FARNESYL CHLORIDE". Paragraph 0090. . Retrieved 2019/12/28.