100896-30-8

Usage

Uses

Used in Cosmetics and Personal Care Products:
(2R)-2-hydroxyoctadecanoic acid methyl ester is used as an ingredient in cosmetics and personal care products for its emollient and moisturizing properties, making it suitable for use in skin and hair care products.
Used in Pharmaceuticals:
(2R)-2-hydroxyoctadecanoic acid methyl ester is used in pharmaceuticals for its versatile applications in the industry.
Used as a Surfactant and Emulsifier:
(2R)-2-hydroxyoctadecanoic acid methyl ester is used as a surfactant and emulsifier in many formulations, contributing to the stability and effectiveness of various products.
Used in Chemical Industry:
(2R)-2-hydroxyoctadecanoic acid methyl ester is used in the chemical industry for its diverse applications in the field.

Upstream product

• 186581-53-3 diazomethane 
• 26633-48-7 (2R)-2-hydroxyoctadecanoic acid 
• 67-56-1 methanol 
• 301850-90-8 (R)-2-Hydroxy-octadecanoic acid [(1S,2R)-2,7-dihydroxy-8-methyl-1-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxymethyl)-heptadecyl]-amide 
• 1173113-34-2 1-O-β-D-glucopyranosyl-(2S,3S,4R)-2-[(2'R)-2'-hydroxyoctadecanoylamino]-16-methyl-heptadeca-1,3,4-triol 
• 629-22-1 2-hydroxystearic acid 
• 1363377-88-1 1-O-β-D-glucopyranosyl-(2S,3S,4E,9E)-2-[(2R)-2-hydroxyoctadecanoylamino]-10-methyl-octadeca-4,9-diene-1,3-diol 
• 1442100-89-1 (2R)-N-{(1S,2R,3E,7E)-1-[(β-D-glucopyranosyloxy)methyl]-2-hydroxy-8-methylhexadeca-3,7-dien-1-yl}-2-hydroxyoctadecanamide 
• 113773-89-0 cerebroside 

Downstream Products

• 506-12-7 heptadecanoic acid 
• 1731-92-6 methyl margarate 

Relevant academic research and scientific papers

Flavusides A and B, antibacterial cerebrosides from the marine-derived fungus Aspergillus flavus

Flavusides A (1) and B (2), two new antibacterial cerebroside derivatives, and the previously described phomaligol A (3), kojic acid (4), methyl kojic acid (5), and dimethyl kojic acid (6) have been isolated from the extract of a marine isolate of the fungus Aspergillus flavus. The structure and absolute stereochemistry of two cerebrosides were assigned on the basis of NMR and Tandem FAB-MS/MS experiments. Compounds 1, 2, and 3 exhibited a mild antibacterial activity against Staphylococcus aureus, methicillin-resistant S. aureus, and multidrug-resistant S. aureus. The minimum inhibitory concentration (MIC) values for each strain are as follows: compounds 1 and 2 showed 15.6 μg/ml for S. aureus and 31.2 μg/ml for methicillin-resistant S. aureus and multidrug-resistant S. aureus, and compound 3 exhibited 31.2 μg/ml for S. aureus and methicillin-resistant S. aureus and 62.5 μg/ml for multidrug-resistant S. aureus.

Impact of free hydroxylated and methyl-branched fatty acids on the organization of lipid membranes

Differential scanning calorimetry (DSC) has been applied to study the effect of free hydroxylated and methyl-branched fatty acids on the physico-chemical properties of lipid membranes. First, the impact of free hydroxy fatty acids (HFAs) on dimyristoylphosphatidylcholine (DMPC) model membranes was monitored only as a function of chain length and position of the attached hydroxyl group. Second, racemic vs. enantiopure anteiso fatty acids (AFAs) and HFAs were investigated to address the question of which role does a fatty acid's chirality play on its membrane pertubing effect. The DSC thermograms revealed that the main gel to liquid-crystalline phase transition of the DMPC bilayers which results in a disordering effect of the lipid hydrocarbon chains was affected in different ways depending on the nature of the incorporated fatty acid. Long-chain 2- and 3-HFAs stabilized the gel phase by reducing the phase transition temperature (Tm), whereas short-chain HFAs and long-chain HFAs with the hydroxy group remote from the head group stabilized the more disordered liquid-crystalline state. Additionally, we observed that enantiopure (S)-14-methylhexadecanoic acid ((S)-a17:0) and (R)-2-hydroxy octadecanoic acid and the corresponding racemates had contrary effects upon incorporation into DMPC bilayers. In both cases, the pure enantiomers alleviated the liquid-crystalline state of the biological model membrane.

Neritinaceramides A-E, new ceramides from the marine bryozoan Bugula neritina inhabiting South China Sea and their cytotoxicity

Five new ceramides, neritinaceramides A (1), B (2), C (3), D (4) and E (5), together with six known ceramides (6-11), two known alkyl glycerylethers (12 and 13) and a known nucleoside (14), were isolated from marine bryozoan Bugula neritina, which inhabits the South China Sea. The structures of the new compounds were elucidated as (2S,3R,3′S,4E,8E,10E)-2-(hexadecanoylamino)- 4,8,10-octadecatriene-l,3,3′-triol (1), (2S,3R,2′R,4E,8E,10E)-2- (hexadecanoylamino)-4,8,10-octadecatriene-l,3,2′-triol (2), (2S,3R,2′R,4E,8E,10E)-2-(octadecanoylamino)-4,8,10-octadecatriene-l,3, 2′-triol (3), (2S,3R,3′S,4E,8E)-2-(hexadecanoylamino)-4,8- octadecadiene-l,3,3′-triol (4) and (2S,3R,3′S,4E)-2- (hexadecanoylamino)-4-octadecene-l,3,3′-triol (5) on the basis of extensive spectral analysis and chemical evidences. The characteristic C-3′S hydroxyl group in the fatty acid moiety in compounds 1, 4 and 5, was a novel structural feature of ceramides. The rare 4E,8E,10E-triene structure in the sphingoid base of compounds 1-3, was found from marine bryozoans for the first time. The new ceramides 1-5 were evaluated for their cytotoxicity against HepG2, NCI-H460 and SGC7901 tumor cell lines, and all of them exhibited selective cytotoxicity against HepG2 and SGC7901 cells with a range of IC 50 values from 47.3 μM to 58.1 μM. These chemical and cytotoxic studies on the new neritinaceramides A-E (1-5) added to the chemical diversity of B. neritina and expanded our knowledge of the chemical modifications and biological activity of ceramides.

Cytotoxic ceramides from the Red Sea sponge Spheciospongia vagabunda

Extracts of Egyptian marine organisms from the Red Sea were screened for their anticancer activity using sulforhodamine B assay. The extract of the Red Sea sponge Spheciospongia vagabunda possessed promising anticancer activity against HepG2 (liver cancer cell line) and MCF-7 (breast cancer cell line). Isolation of three new ceramides: N-[(2S,3S,4R)-1,3,4-trihydroxytetradecan-2-yl] tridecanamide (1), (R)-2′-hydroxy-N-[(2S,3S,4R)-1,3,4-trihydroxypentacosan-2-yl] octadecanamide (2) and (R,Z)-2′-hydroxy-N-[(2S,3S,4R)-1,3,4-trihydroxytricosan-2-yl) nonadec-10-enamide (3) was accomplished via bioassay-guided fractionation. Structure elucidation was achieved using spectroscopic techniques, including 1D and 2D NMR and HRMS. Compounds 2 and 3 displayed high potential cytotoxicity against HepG2 (IC50 24.7 and 21.3 μM, respectively) and MCF-7 (IC50 26.8 and 29.8 μM, respectively), compared with doxorubicin as control drug.

The antitumor constituents from hedyotis diffusa willd

As a TCM, Hedyotis diffusa Willd. has been using to treat malignant tumors, and many studies also showed that the extracts from Hedyotis diffusa Willd. possessed evident antitumor activities. Therefore, we carried out chemical study on Hedyotis diffusa Willd. and investigated the cytotoxicity of the obtained compounds on a panel of eight tumor cell lines. As a result, four new compounds were isolated from Hedyotis diffusa Willd., including three iridoid glycosides of Shecaoiridoidside A-C (1-3) and a cerebroside of shecaocerenoside A (4). Also, six known iridoid compounds (5-10) were also obtained. The cytotoxicity of all compounds against human tumor cell lines of HL-60, HeLa, HCT15, A459, HepG2, PC-3, CNE-2, and BCG-823 were also evaluated in vitro. New compound 3 exhibited evident cytotoxicity to all tumor cell lines except the Hela, and the IC50 values are from 9.6 μ M to 62.2 μ M, while new compound 4 showed moderate cytotoxicity to all the cell lines, and the IC50 values are from 33.6 μ M to 89.3 μ M. By contrast, new compound 1 and known compound 9 showed moderate cytotoxicity to HCT15, A459, and HepG2 selectively. Known compound 7 also exhibited moderate cytotoxicity to HCT15 and A459 selectively.

New cerebrosides from a marine sponge Haliclona (Reniera) sp

A chemical investigation of the MeOH extract of a marine sponge Haliclona (Reniera) sp., collected off the coast of Ulleung Island, Korea, led to the isolation of thirteen new cerebrosides (1-3, 5-14), along with a known analogue (4). Their structures wer

Termitomycesphins A-D, novel neuritogenic cerebrosides from the edible Chinese mushroom Termitomyces albuminosus

Four novel cerebrosides, termitomycesphins A-D, were isolated from the edible Chinese mushroom Termitomyces albuminosus (Berk.) Heim. ('Jizong' in Chinese), shown to induce neuronal differentiation in rat PC12 cells. The absolute stereostructures were elucidated by spectroscopic methods and chemical derivatization. These new cerebrosides have a unique C19 hydroxylated sphingosine base with branching around the middle. Termitomycesphins A and C possessing a C16 α-hydroxy fatty acid showed a higher neuritogenic activity than did termitomycesphins B and D possessing a C18 α-hydroxy fatty acid. (C) 2000 Elsevier Science Ltd.

Novel cerebrosides isolated from the fermentation mycelia of tuber indicum

The four new cerebrosides 1-4 possessing a unique C18 9-methylsphinga-4,8-dienine-related moiety and a cyclic octapeptide, 5, possessing alternating proline and glycine moietes were isolated from the Tuber indicum fermentation mycelium. Their structures were established on the basis of a spectroscopic analysis including NMR and HR-ESI-MS, as well as an acidic methanolysis experiment. To the best of our knowledge, the cerebrosides identified in the present study are quite different from those isolated from Tuber indicum fruiting bodies. Additionally, it was the first time that a cyclic peptide was isolated from the Tuber genus. Copyright

Two cerebrosides and one acylglycosyl sterol from Monochoria vaginalis

Three new compounds have been isolated from the whole plant of Monochoria vaginalis and characterized as: (2S,3R,4E,8E,2′R)-1-O-(β-D- glucopyranosyl)-N-(2′-hydroxyicosanoyl)-4,8-sphingadienine, (2S,3R,4E,8E,2′R)-1-O-(β-D-glucopyranosyl)-N-(2′- hydroxyocta

Cerebrosides from Fomitopsis pinicola (Sw. Ex Fr.) Karst.

A cerebroside fraction was obtained from the bruit bodies of fomitopsis pinicola using column chromatography and then separated into six compounds by reversed-phase HPLC.The sugar component of all cerebrosides was D-glucose.The major fatty acids were 2-hydroxyfatty acids (C14-C18), the long chain base was identified as 9-methyl-C18-4,8-sphingadienine which is widely distributed in fungi and reported to be essential for the fruit-inducing activity of fungi.Based on degradation studies, fast atom bombardment mass spectrometry, and different 1H and 13C NMR investigations, the structure of the main cerebroside (1) was determined to be (4E,8E,2S,3R,2'R)-N-2'-hydroxypalmityl-1-O-β-D-glucopyranosyl-9-methyl-4,8-sphingadienine. - Keywords: Cerebroside; Glycolipid; Fomitopsis pinicola; 1H and 13C NMR