CAS 122-32-7 Triolein - Vaccine Lab / Alfa Chemistry

Triolein and Graphene in the Development of High-Temperature Resistant Lubricants

A novel graphene/triolein complex-based lubricant for improving high temperature water-based drilling fluid Geng Y, et al. RSC Advances, 2023, 13(49), 34772-34781.

Triolein has garnered significant attention as an eco-friendly diesel lubricant additive, owing to its exceptional lubrication properties, thermal stability, and consistent performance across a wide temperature range. Incorporating graphene into triolein has been shown to markedly enhance the lubrication properties of drilling fluids, leading to the creation of a high-temperature resistant lubricant.
The preparation process involves the following steps:
An appropriate amount of graphene and triolein is weighed at a mass ratio of 1:4. The graphene is then added to the triolein, and the mixture is stirred until the graphene is evenly dispersed. The mixture is heated to 60°C, maintaining this temperature with continuous stirring, ensuring uniform dispersion of graphene within the triolein matrix. The process is complete when a homogeneous black solution is obtained.

A Green Approach to Biogasoline Production from Triolein

Transformation of triolein to biogasoline by photo-chemo-biocatalysis Xu W, et al. Green Chemistry, 2022, 24(17), 6589-6598.

In this study, a novel photo-chemo-enzymatic multi-step method was developed for the efficient and eco-friendly production of biogasoline from the sustainable lipid triolein. Unlike traditional methods that require harsh reaction conditions, this approach utilizes solar energy and atmospheric oxygen (O₂) under mild conditions, making it an environmentally friendly alternative.
The process begins with the lipase-catalyzed hydrolysis of triolein, breaking it down into its component fatty acids. This is followed by the decarboxylation of oleic acid, catalyzed by fatty acid photodecarboxylase (CvFAP). Next, the long-chain alkene undergoes photocatalytic oxidative cleavage, which is then followed by the CvFAP mutant-catalyzed decarboxylation of medium- or short-chain fatty acids. This sequential reaction, optimized through detailed experimentation, successfully converts triolein into biogasoline.
The practicality of this method was demonstrated through a gram-scale experiment, proving its effectiveness on a larger scale. Moreover, the protocol was successfully applied to convert various long-chain unsaturated acids and alkenes into biogasoline, highlighting its broad substrate scope.

Triolein Used to Prepare Triolein-embedded Cellulose Acetate Membrane (TECAM)

Accumulation and passive sampling of bisphenol analogues using triolein-embedded cellulose acetate membrane in waters Gao X, et al. Science of The Total Environment, 2021, 798, 148985.

Triolein-embedded cellulose acetate membrane (TECAM) is created by incorporating triolein into a cellulose acetate membrane. This membrane effectively accumulates hydrophobic bisphenol analogs (BP), making it a valuable passive sampler for monitoring hydrophobic and moderately hydrophilic organic pollutants in water.
The preparation of TECAM follows the Loeb-Sourirajan technique. A homogeneous solution is prepared by dissolving cellulose acetate (17.5 wt %) in a solvent mixture of acetone (69 wt %) and 1,4-dioxane (10 wt %), along with the additives anhydrous magnesium perchlorate (2 wt %) and triolein (1.5 wt %). This mixture is subjected to ultrasonic oscillation for 30 minutes and then allowed to rest at 25 °C overnight.
To achieve the desired membrane thickness, the solution is cast onto a glass plate by spreading it between thin wires (200 μm diameter) using a glass stick. After allowing the solvent to evaporate for 60 seconds at 20 °C, the membranes are immersed in a distilled water coagulation bath (20 °C) for at least 10 minutes to ensure complete phase separation. Finally, the membranes are thoroughly rinsed with distilled water.

Triolein as a Photoprotective Agent Against UVB-Induced Skin Damage

Triolein reduces MMP-1 upregulation in dermal fibroblasts generated by ROS production in UVB-irradiated keratinocytes Leirós GJ, et al. Journal of Dermatological Science, 2017, 85(2), 124-130.

Ultraviolet B (UVB) radiation is a primary contributor to skin photoaging, primarily through cytokine production and oxidative stress in the skin. UVB-induced interleukin-6 (IL-6) production in keratinocytes plays a significant role in upregulating metalloproteinases (MMPs) in dermal fibroblasts, leading to collagen breakdown and skin aging.
This study investigated the potential of triolein to mitigate UVB-induced skin damage by assessing its effect on MMP1 (interstitial collagenase) expression in dermal fibroblasts. The key focus was on how triolein impacts IL-6 expression and reactive oxygen species (ROS) generation in UVB-irradiated keratinocytes.
The research demonstrated that UVB irradiation of keratinocytes significantly increased IL-6 expression and ROS production, leading to an upregulation of MMP1 mRNA expression in fibroblasts cultured in conditioned medium from these irradiated cells. However, treating keratinocytes with triolein effectively reduced both IL-6 expression and ROS generation. Consequently, this reduction in oxidative stress and inflammation in keratinocytes led to a marked decrease in MMP1 expression in dermal fibroblasts.
The findings suggest that triolein exerts anti-inflammatory and antioxidative effects on UVB-irradiated keratinocytes, which in turn protect dermal fibroblasts from UVB-induced collagen degradation. This study highlights triolein's potential as a photoprotective agent that could be beneficial in preventing skin photoaging by reducing the harmful effects of UVB radiation on the skin.

Catalog Number	ACM122327-3
CAS	122-32-7
Structure
Synonyms	1,2,3-Propanetriyltri-((E)-9-octadecenoate)
IUPAC Name	2,3-Bis[[(Z)-octadec-9-enoyl]oxy]propyl (Z)-octadec-9-enoate
Molecular Weight	885.43
Molecular Formula	C57H104O6
Canonical SMILES	CCCCCCCCC=CCCCCCCCC(=O)OCC(COC(=O)CCCCCCCC=CCCCCCCCC)OC(=O)CCCCCCCC=CCCCCCCCC
InChI	InChI=1S/C57H104O6/c1-4-7-10-13-16-19-22-25-28-31-34-37-40-43-46-49-55(58)61-52-54(63-57(60)51-48-45-42-39-36-33-30-27-24-21-18-15-12-9-6-3)53-62-56(59)50-47-44-41-38-35-32-29-26-23-20-17-14-11-8-5-2/h25-30,54H,4-24,31-53H2,1-3H3/b28-25-,29-26-,30-27-
InChI Key	PHYFQTYBJUILEZ-IUPFWZBJSA-N
Boiling Point	235-240 °C/18 mmHg(lit.)
Melting Point	-5.5 °C
Flash Point	330 °C
Purity	95%+
Density	0.91 g/mL(lit.)
Solubility	Insoluble in water
Appearance	Clear pale yellow liquid
Storage	-20 °C
Complexity	1010
Covalently-Bonded Unit Count	1
Defined Atom Stereocenter Count	0
Exact Mass	884.78329103
Heavy Atom Count	63
Hydrogen Bond Acceptor Count	6
Hydrogen Bond Donor Count	0
Isomeric SMILES	CCCCCCCC/C=C\CCCCCCCC(=O)OCC(OC(=O)CCCCCCC/C=C\CCCCCCCC)COC(=O)CCCCCCC/C=C\CCCCCCCC
Monoisotopic Mass	884.78329103
Physical State	Liquid
Rotatable Bond Count	53
Stability	Stability Stable, but air and light sensitive. Incompatible with strong oxidizing agents.
Storage Conditions	2-8°C
Topological Polar Surface Area	78.9 Å²