927-18-4

Usage

Chemical composition

Consists of a propanediol molecule with an octadecyloxy group attached to one of its carbon atoms.

Usage in personal care and cosmetics

Commonly used in skincare, haircare, and makeup products.

Emollient properties

Softens and smooths the skin by providing a protective barrier and preventing moisture loss.

Surfactant

Acts as a wetting agent, reducing the surface tension of a liquid, allowing it to spread more easily.

Emulsifier

Helps mix two immiscible substances (such as oil and water) by surrounding droplets of one substance with molecules of the other, forming an emulsion.

InChI:InChI=1/C21H44O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-24-21(19-22)20-23/h21-23H,2-20H2,1H3

Upstream product

• 112-89-0 1-Bromooctadecane 
• 112-61-8 Methyl stearate 
• 56-81-5 glycerol 
• 111-03-5 1-monooleoyl glycerol 
• 22610-63-5 octadecanoic acid 2,3-dihydroxypropyl ester 
• 3386-33-2 1-chlorooctadecane 
• 115292-37-0 5-(octadecyloxy)-2-phenyl-1,3-dioxane 
• 629-93-6 n-iodooctadecane 
• 1708-40-3 2-phenyl-[1,3]dioxan-5-ol 
• 82521-21-9 cis-5-(1-octadecyloxy)-2-phenyl-1,3-dioxan 
• 76-84-6 triphenylmethyl alcohol 
• 6972-79-8 dibenzyl glycerol 

Downstream Products

• 13232-26-3 Monostearoyl-β-batylalkohol A 
• 118477-24-0 Ditrityl-β-batylalkohol 

Relevant academic research and scientific papers

Synthesis of bioconjugate sesterterpenoids with phospholipids and polyunsaturated fatty acids

A series of sesterterpenoid bioconjugates with phospholipids and polyunsaturated fatty acids (PUFAs) have been synthesized for biological activity testing as antiproliferative agents in several cancer cell lines. Different substitution analogues of the or

1-O-Alkyl (di)glycerol ethers synthesis from methyl esters and triglycerides by two pathways: Catalytic reductive alkylation and transesterification/reduction

From available and bio-sourced methyl esters, monoglycerides or oleic sunflower refined oil, the corresponding 1-O-alkyl (di)glycerol ethers were obtained in both high yields and selectivity by two different pathways. With methyl esters, a reductive alkylation with (di)glycerol was realized under 50 bar hydrogen pressure in the presence of 1 mol% of Pd/C and an acid co-catalyst. A second two step procedure was evaluated from methyl esters or triolein and consisted of a first transesterification to the corresponding monoglyceride with a BaO/Al2O3 catalyst, then its reduction to the desired glycerol monoether with a recyclable heterogeneous catalytic system Pd/C and Amberlyst 35 under H2 pressure. In addition, a mechanism for the reaction was also proposed.

Sterol-modified phospholipids: Cholesterol and phospholipid chimeras with improved biomembrane properties

We synthesized a family of sterol-modified glycerophospholipids (SML) in which the sn-1 or sn-2 position is covalently attached to cholesterol and the alternative position contains an aliphatic chain. The SML were used to explore how anchoring cholesterol to a phospholipid affects cholesterol behavior in a bilayer. Notably, cholesterol in the SML retains the membrane condensing properties of free cholesterol regardless of the chemistry or position of its attachment to the glycerol moiety of the phospholipid. SMLs by themselves formed liposomes upon hydration and in mixtures between an SML and diacylglycerophospholipids (C14 to C18 chain length) the thermotropic phase transition is eliminated at the SML equivalent of about 30 mol % free cholesterol. Osmotic-induced contents leakage from SML (C14-C18) liposomes depends upon the linkage and position of cholesterol but in general is similar to that observed in 3/2 diacylphosphatidylcholine/cholesterol (mole ratio) liposomes. SML liposomes are exceptionally resistant to contents release in the presence of serum at 37°C. This is probably due to the fact that SML exchange between bilayers is more than 100 fold less than the exchange rate of free cholesterol in the same conditions. Importantly, SML liposomes containing doxorubicin are as effective in treating the murine C26 colon carcinoma as Doxil, a commercial liposome doxorubicin formulation. SMLs stabilize bilayers but do not exchange and hence provide a new tool for biophysical studies on membranes. They may improve liposomal drug delivery in organs predisposed to the extraction of free cholesterol from bilayers, such as the skin, lung, or blood.

Unique spirocyclopiperazinium salt. Part 2: Synthesis and structure-activity relationship of dispirocyclopiperazinium salts as analgesics

Three series of spirocyclopiperazinium derivatives 5a-d, 6a-f and 17a-d were synthesized and evaluated for their in vivo analgesic activities. Compounds 5a, 17a and 17b exhibited excellent analgesic activity. Two important structure-activity relationships were observed from this study: (1) the quaternary ammonium functionality is a critical pharmacophore for analgesic activity; (2) it is important to adjust the lipophilic property of compounds to improve analgesic activity.

Heteroaryl-substituted deoxy glycerols and antibacterial and antiviral compositions containing the same

Heteroaryl-substituted deoxy glycerols represented by the general Formulas Ia, Ib and Ic: STR1 wherein: X is oxygen (--O--) or sulfur (--S--); R is substituted or unsubstituted straight or branched chain C1-30 alkyl or alkenyl, provided that a double bond of the alkenyl does not originate at the carbon atom bound to the X substituent; Het is a 5- to 9-membered heteroaryl mono- or bicyclic ring system having no more than 1 carbonyl carbon in the ring system, with 1 to 4 nitrogen atoms as the sole heteroatoms, one of which nitrogens is bonded to the glycero carbon; and Y is hydroxyl (--OH) or thiol (--SH), pharmaceutical compositions containing the same, and methods of using the compounds, are disclosed. The compounds exhibit antiviral and antibacterial activities.

Heteroaryl-Substituted Deoxy Glycero-Phosphoethanolamines

Therapeutically active, heteroaryl-substituted deoxy glycero-phosphoethanolamines are disclosed having the general Formula I: STR1 wherein one of X, Y or Z is a fatty ether substituent, one is a heteroaryl ring substituent with 1-4 nitrogens as the only heteroatoms, one of which is bonded to a carbon of the glyceryl backbone, and one is a phosphoethanolamine substituent substituted at the nitrogen, provided that each of X, Y and Z is a different substituent, and the pharmaceutical compositions comprising the therapeutically active compounds and methods of using the therapetically active compounds to treat cancerous tumors, psoriasis and inflammation are also disclosed.

Diene-Containing Lipids as Probes for Phase-Transition Behavior of Lipids in Liposomes

The absorption maximum (λmax) of 1,2-bis(2,4-octadecadienoyl)-sn-glycero-3-phosphorylcholine (DODPC), dispersed in an aqueous medium as liposomes, showed blue shift from 256.8 nm to 241.8 nm when these liposomes were cooled down from liquid crystalline state to gel state.The blue shift is explained to be due to stronger interaction between diene groups at gel state.This diene-containing lipid is examined to be an excellent membrane probe because it is typical phopholipid and miscible with several lipids.Furthermore, the dienoyl groups are known to be settled in the definite positions in bilayer membrane by suitable chemical modification.Phase transition behaviors of various 2,4-octadecadienoyl-containing phosphorylcholines as analogs for DODPC have also been investigated.Although they had similar spectral shifts at gel-to-liquid crystalline phase-transition temperature, their phase-transition temperatures and magnitude of λmax shifts were revealed to be related directly and therefore be governed by the different packing of the diene groups in bilayer membrane.DODPC was mixed with 1,2-dipalmitoyl-sn-glycero-3-phosphorylcholine, or cholesterol, and phase behaviors of these mixed liposomes were also examined.Phase-transition of the mixed liposomes was detected easily by the shift of its λmax with high sensitivity.Results were quite comparable to those obtained from other measurements, such as DSC, NMR, and so on.

1,3(R):4,6(R)-DI-O-BENZYLIDEN-D-MANNIT ALS AUSGANGSPRODUKT FUER DIE SYNTHESE OPTISCH AKTIVER GLYCERIN-DERIVATE

Starting from the di-O-benzylidene-D-mannitol derivative 11, certain types of optically active glycerol derivatives can be prepared with a minimum of protecting group chemistry.This is exemplified by an efficient synthesis of 2-O-alkyl glyceric acid derivatives 22 and 23.