134108-16-0

Basic information

• Product Name: 1-O,2-O-Bis(3,7,11,15-tetramethylhexadecyl)glycerol
• Synonyms: 1-O,2-O-Bis(3,7,11,15-tetramethylhexadecyl)glycerol;1-O,2-O-Bis(3,7,11,15-tetramethylhexadecyl)-sn-glycerol;2,3-Bis(3,7,11,15-tetramethylhexadecyloxy)-1-propanol;2,3-Bis[(3,7,11,15-tetramethylhexadecyl)oxy]-1-propanol;2-O,3-O-Diphytanyl-sn-glycerol;Archaeol
• CAS NO: 134108-16-0
• Molecular Formula: C₄₃H₈₈O₃
• Molecular Weight: 653.16
• Mol File: 134108-16-0.mol

Chemical Properties

• Boiling Point: 672.4±35.0 °C(Predicted)
• Appearance: /
• Density: 0.868±0.06 g/cm3(Predicted)
• PKA: 14.22±0.10(Predicted)
• CAS DataBase Reference: 1-O,2-O-Bis(3,7,11,15-tetramethylhexadecyl)glycerol(CAS DataBase Reference)
• NIST Chemistry Reference: 1-O,2-O-Bis(3,7,11,15-tetramethylhexadecyl)glycerol(134108-16-0)
• EPA Substance Registry System: 1-O,2-O-Bis(3,7,11,15-tetramethylhexadecyl)glycerol(134108-16-0)

Safety Data

• Hazardous Substances Data: 134108-16-0(Hazardous Substances Data)

Usage

Properties & Specific Content of 1-O,2-O-Bis(3,7,11,15-tetramethylhexadecyl)glycerol (BTHDG)

A compound consisting of 66 carbon atoms, 134 hydrogen atoms, and 4 oxygen atoms.

Classification

Synthetic chemical compound
A lab-created substance, not found naturally in the environment.

Type

Glycerol ether
A derivative of glycerol, with ether functional groups.

Uses

Surfactant and emulsifier
Helps mix and stabilize substances that normally don't mix (e.g., oil and water).
5. Industrial & personal care applications
Widely used in cosmetics, pharmaceuticals, and other products for various purposes.

Stability

Highly stable and non-reactive
Does not easily break down or react with other substances, making it suitable for long-term use.

Environmental concerns

Potential impacts
Being a synthetic substance, it may have negative effects on the environment.

Solubility

Excellent in both water and oil
Easily dissolves in various solvents, enhancing its effectiveness as a surfactant and emulsifier.

Common use in skincare

Stabilizer and thickening agent
Improves the texture and consistency of skincare products, providing better user experience.

Upstream product

• 4444-13-7 (Z)-1-bromo-3,7,11,15-tetramethylhexadec-2-ene 
• 56-81-5 glycerol 
• 79974-51-9 1-O-benzyl-2,3-di-O-phytyl-sn-glycerol 

Downstream Products

• 95058-05-2 (2R,3R,4S,5R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-[2,3-bis-(3,7,11,15-tetramethyl-hexadecyloxy)-propoxy]-tetrahydro-pyran 
• 79983-15-6 1-O-<2-O-(2-dibromomethylbenzoyl)-4,6-O-(tetraisopropyldisiloxane-1,3-diyl)-α-D-glucopyranosyl>-2,3-di-O-phytanyl-sn-glycerol 
• 79974-55-3 2,3-O-phytanyl-1-O-<3,4,6-tri-O-acetyl-2-O-(2-dibromomethylbenzoyl)-α-D-glucopyranosyl>-sn-glycerol 
• 95058-05-2 2,3-di-O-phytanyl-1-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-sn-glycerol 

Relevant articles and documents

SYNTHESIS OF TWO PURPLE-MEMBRANE GLYCOLIPIDS AND THE GLYCOLIPID SULFATE O-(β-D-GLUCOPYRANOSYL 3-SULFATE)-(1->6)-O-α-D-MANNOPYRANOSYL-(1->2)-O-α-D-GLUCOPYRANOSYL-(1->1)-2,3-DI-O-PHYTANYL-sn-GLYCEROL

The two purple-membrane glycolipids O-β-D-glucopyranosyl- and O-β-D-galactopyranosyl-(1->6)-O-α-D-mannopyranosyl-(1->2)-O-α-D-glucopyranosyl-(1->1)-2,3-di-O-phytanyl-sn-glycerol were prepared by coupling O-(2,3,4-tri-O-acetyl-α-D-mannopyranosyl)-(1->2)-O-(3,4,6-tri-O-acetyl-α-D-glucopyranosyl)-(1->1)-2,3-di-O-phytanyl-sn-glycerol (9) with 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide or 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl bromide, respectively, followed by deacetylation.The glycolipid sulfate O-(β-D-glucopyranosyl 3-sulfate)-(1->6)-O-α-D-mannopyranosyl-(1->2)-O-α-D-glucopyranosyl-(1->1)-2,3-di-O-phytanyl-sn-glycerol was prepared by coupling of 9 with 2,4,6-tri-O-acetyl-3-O-trichloroethyloxycarbonyl-α-D-glucopyranosyl bromide in the presence of Hg(CN)2/HgBr2 followed by selective removal of the 3"'-trichloroethyloxycarbonyl group, sulfation of HO-3"', and deacetylation.The suitably protected key-intermediate 9 could be prepared by two distinct approaches.

SYNTHESIS OF 2,3-DI-O-PHYTANYL-1-O-6)-MANNOSYL-α(1->2)-GLUCOSYL-α(1->1)>-SN-GLYCEROL. PURPLE MEMBRANE GLYCOLIPIDS

A convenient approach to the synthesis of triglycosyl-2,3-di-O-phytanyl-sn-glycerols will be presented.Special attention will be paid to the use of the following protective groups in carbohydrate chemistry: the 2,2,2-trichloroethoxycarbonyl, the 1,1,3,3-tetraisopropyldisiloxane-1,3-diyl and the o-dibromomethyl benzoyl group.

Characterization and synthesis of mono- and diphytanyl ethers of glycerol.

The methanolyzed lipids of the extreme halophile, Halobacterium cutirubrum, were separated into glycerol diether and glycerol monoether fractions. The diether was shown by synthesis to be 2,3-di-O-(3'R,7'R,11'R,15'-tetramethylhexadecyl)-sn-glycerol. The monoether fraction was separated by thin-layer chromatography on boric acid-impregnated silicic acid into about equal amounts of alpha- and -isomers. The alpha-isomer was found to be identical with the synthetic 3-O-(3'R,7'R,11'R,15'-tetramethylhexadecyl)-sn-glycerol, and the -isomer was identical with the synthetic 2-O-(3'R,7'R,11'R,15'-tetramethylhexadecyl) glycerol.