Maslinic acid

472.70000

472.70

610-137-3

E233J88OHQ

Crystalline solid

2940000000

77.76000

6.5

Solid

1.14g/cm3

255-258 °C

570ºC at 760 mmHg

312.6ºC

1.568

acetone: soluble 1mg/mL, clear, colorless;Sparingly soluble in aqueous buffers

2.3X10-15 mm Hg at 25 deg C (est)

Henry's Law constant = 3.5X10-11 atm-cu m/mol at 25 °C (est)

pKa = 4.81 (est)

Hydroxyl radical reaction rate constant = 1.3X10-10 cu cm/molecule-sec at 25 °C (est)

NONH for all modes of transport

3

24/25

SRP: Criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.|SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a permitted wastewater treatment facility is acceptable only after review by the governing authority and assurance that "pass through" violations will not occur. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must be evaluated in accordance with EPA 40 CFR Part 261, specifically Subpart B, in order to determine the appropriate local, state and federal requirements for disposal.

Safety glasses, latex disposable gloves|Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower.|Use process enclosures, local exhaust ventilation, or other engineering controls to control airborne levels below recommended exposure limits.

As in any fire, wear self-contained breathing apparatus pressure-demand (MSHA-NIOSH approved or equivalent), and full protective gear to prevent contact with skin and eyes.|Use alcohol-resistant foam, carbon dioxide, water, or dry chemical spray when fighting fires involving this material.

Steps to be taken in case material is released or spilled: Wear a NIOSH/MSHA approved self-contained breathing apparatus and appropriate personal protection (rubber boots, safety goggles, and heavy rubber gloves). Vacuum or sweep up material and place in disposal container. Avoid breathing dust. After removal, ventilate contaminated area and flush thoroughly with water.

Wash thoroughly after handling.|SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. The completeness of the cleaning procedures should be considered before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at the end of shift, but should remain at employee's place of work for cleaning.

Maslinic acid is found in a number of natural sources, most notably pomace olive oil (orujo)(1). Maslinic acid occurs in red dates, olives, camellia, pomegranate and sage(2).

Maslinic acid's production and use as a dietary supplement and as an ingredient in consumer products such as olive oil and skin care lotion products(1) may result in its release to the environment through various waste streams(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1270(SRC), determined from an estimated log Kow of 6.82(2) and a regression-derived equation appropriate for ionizable compounds(2), indicates that maslinic acid is expected to have low mobility in soil(SRC). The estimated pKa of maslinic acid is 4.81(3), indicating that this compound will exist partially in anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4). Volatilization of maslinic acid from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 3.5X10-11 atm-cu m/mole(SRC) using a fragment constant estimation method(2). Maslinic acid is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2.3X10-15 mm Hg at 25 °C(SRC) determined from a fragment constant method(2). Biodegradation data in soil were not available(SRC, 2012).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1270(SRC), determined from an estimated log Kow of 6.82(2) and a regression-derived equation appropriate for ionizable compounds(2), indicates that maslinic acid is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 3.5X10-11 atm-cu m/mole(SRC) developed using a fragment constant estimation method(2). According to a classification scheme(4), an estimated BCF of 56(SRC), from an estimated log Kow of 6.82(2) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is moderate(SRC). Maslinic acid is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3). Maslinic acid contains a cyclic olefin and cyclic olefins can undergo sensitized photo-oxidation in surface waters exposed to sunlight via reaction with hydroxyl, singlet oxygen and RO2 radicals with half-lives on the order of 13 to 40 days at the water surface(5); therefore, photo-oxidation may be an important fate process for maslinic acid in natural water(SRC). Biodegradation data in water were not available(SRC, 2012).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), maslinic acid, which has an estimated vapor pressure of 2.3X10-15 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase maslinic acid may be removed from the air by wet and dry deposition(SRC).

The rate constant for the vapor-phase reaction of maslinic acid with photochemically-produced hydroxyl radicals has been estimated as 1.3X10-10 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 3 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Maslinic acid is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(2). Maslinic acid contains a cyclic olefin and cyclic olefins can undergo sensitized photo-oxidation in surface waters exposed to sunlight via reaction with hydroxyl, singlet oxygen and RO2 radicals with half-lives on the order of 13 to 40 days at the water surface(3); therefore, photo-oxidation may be an important fate process for maslinic acid in natural water(SRC).

An estimated BCF of 56 was calculated in fish for maslinic acid(SRC) using an estimated log Kow of 6.82(1) and a regression-derived equation(1). According to a classification scheme(2), this BCF suggests the potential for bioconcentration in aquatic organisms is moderate(SRC).

The Koc of maslinic acid is estimated as 1270(SRC), using an estimated log Kow of 6.82(1) and a regression-derived equation appropriate for an ionizable compound(1). According to a classification scheme(2), this estimated Koc value suggests that maslinic acid is expected to have low mobility in soil. The estimated pKa of maslinic acid is 4.81(3), indicating that this compound will exist partially in anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4).

The Henry's Law constant for maslinic acid is estimated as 3.5X10-11 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that maslinic acid is expected to be essentially nonvolatile from water surfaces(2). Maslinic acid's Henry's Law constant indicates that volatilization from moist soil surfaces is not expected to occur(SRC). Maslinic acid is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2.3X10-15 mm Hg(SRC) determined from a fragment constant method(1).

Occupational exposure to maslinic acid may occur through dermal contact with this compound at workplaces where maslinic acid is produced or used. The general population is exposed to maslinic acid via ingestion of dietary supplements and foods containing maslinic acid, especially olive oil, and dermal contact with this compound in consumer products containing maslinic acid such skin care lotion products. (SRC)

Maslinic acid, a pentacyclic triterpene found in the protective wax-like coating of the leaves and fruit of Olea europaea L., is a promising agent for the prevention of colon cancer. Investigators have shown /previously/ that maslinic acid inhibits cell proliferation to a significant extent and activates mitochondrial apoptosis in colon cancer cells. /This study/ investigated... this compound's apoptotic molecular mechanism. /Investigators/ used HT29 adenocarcinoma cells. Changes /in/ genotoxicity were analyzed by single-cell gel electrophoresis (comet assay). The cell cycle was determined by flow cytometry. Finally, changes in protein expression were examined by western blotting. Student's t-test was used for statistical comparison. HT29 cells treated with maslinic acid showed significant increases in genotoxicity and cell-cycle arrest during the G0/G1 phase after 72 hours treatment and an apoptotic sub-G0/G1 peak after 96 hours... the anti-tumoral activity of maslinic acid might proceed via p53-mediated apoptosis by acting upon the main signaling components that lead to an increase in p53 activity and the induction of the rest of the factors that participate in the apoptotic pathway. /Investigators/ found that in HT29 cells maslinic acid activated the expression of c-Jun NH2-terminal kinase (JNK), thus inducing p53. Treatment of tumor cells with maslinic acid also resulted in an increase in the expression of Bid and Bax, repression of Bcl-2, release of cytochrome-c and an increase in the expression of caspases -9, -3, and -7. Moreover, maslinic acid produced belated caspase-8 activity, thus amplifying the initial mitochondrial apoptotic signaling. All these results suggest that maslinic acid induces apoptosis in human HT29 colon-cancer cells through the JNK-Bid-mediated mitochondrial apoptotic pathway via the activation of p53...|Maslinic acid (2-alpha, 3-beta-dihydroxyolean-12-en-28-oic acid) is a natural triterpenoid compound from Olea europaea. This compound prevents oxidative stress and pro-inflammatory cytokine generation in vitro. This study ...investigated the anti-inflammatory effects of maslinic acid in central nervous system by using rat astrocyte cultures stimulated with lipopolysaccharide (LPS). /It/ evaluated different proteins implicated in the nuclear factor kappa B (NF-kappa B) signal transducer pathway employing Western blot and quantitative real time PCR techniques. Results demonstrated that maslinic acid treatment exerted potent anti-inflammatory action by inhibiting the production of Nitric Oxide and tumor necrosis factor alpha (TNF-alpha). Western blot analysis showed that maslinic acid treatment attenuated LPS-induced translocation of NF-kappa B p65 subunit to the nucleus and prevented LPS-induced I kappa B alpha phosphorylation in a concentration-dependent manner, Moreover, maslinic acid significantly suppressed the expression of cyclooxygenase 2 (COX-2) and inducible nitric oxide synthase (iNOS) at protein and mRNA levels. These results suggest that maslinic acid can potentially reduce neuroinflammation by inhibiting NF-kappa B signal transducer pathway in cultured cortical astrocytes.|Activation of NF-kappaB and MAPK/activator protein 1 (AP-1) signaling pathways by receptor activator NF-kappaB ligand (RANKL) is essential for osteoclast activity. Targeting NF-kappaB and MAPK/AP-1 signaling to modulate osteoclast activity has been a promising strategy for osteoclast-related diseases. /This study/ examined the effects of maslinic acid (MA), a pentacyclic triterpene acid that is widely present in dietary plants, on RANKL-induced osteoclastogenesis, osteoclast function, and signaling pathways by in vitro and in vivo assay systems. In mouse bone marrow monocytes (BMMs) and RAW264.7 cells, MA inhibited RANKL-induced osteoclastogenesis in a dose-dependent manner within nongrowth inhibitory concentration, and MA decreased osteoclastogenesis-related marker gene expression, including TRACP, MMP9, c-Src, CTR, and cathepsin K. Specifically, MA suppressed osteoclastogenesis and actin ring formation at early stage. In ovariectomized mice, administration of MA prevented ovariectomy-induced bone loss by inhibiting osteoclast activity. At molecular levels, MA abrogated the phosphorylation of MAPKs and AP-1 activity, inhibited the Ikappa Balpha phosphorylation and degradation, blocked NF-kappaB/p65 phosphorylation, nuclear translocation, and DNA-binding activity by downregulating RANK expression and blocking RANK interaction with TRAF6. Together /this/ data demonstrate that MA suppresses RANKL-induced osteoclastogenesis through NF-kappa B and MAPK/AP-1 signaling pathways and that MA is a promising agent in the treatment of osteoclast-related diseases such as osteoporosis.

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/|/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/

/ALTERNATIVE and IN VITRO TESTS/ Olives and their derivatives represent an important component of the Mediterranean diet that has been considered to be protective against cancer... the effect on cell proliferation and apoptosis in HT-29 cells of an extract from the skin of olives composed of pentacyclic triterpenes with the main components maslinic acid (73.25%) and oleanolic acid (25.75%) was investigated. Studies of the dose-dependent effects showed antiproliferative activity at an EC50 value of 73.96 +/- 3.19 uM/L of maslinic acid and 26.56 +/- 2.55 uM/L of oleanolic acid without displaying necrosis. Apoptosis was confirmed by the microscopic observation of changes in membrane permeability in 40.9 +/- 3.9% and detection of DNA fragmentation in 24.5 +/- 1.5% of HT-29 cells incubated for 24 hr with olive fruit extract containing 150 and 55.5 uM/L of maslinic and oleanolic acids, respectively. Caspase-3 was activated in a dose-dependent manner after incubation for 24 hr. The extract containing 200 uM/L maslinic acid and 74 uM/L oleanolic acid increased caspase-3-like activity to 6-fold that of control cells. Programmed cell death was induced by the intrinsic pathway, as evidenced by the production of superoxide anions in the mitochondria of cells treated with olive fruit extracts containing 150 and 55.5 uM/L of maslinic and oleanolic acids, respectively...|/ALTERNATIVE and IN VITRO TESTS/ Protein kinase C (PKC) has been implicated in carcinogenesis and displays variable expression profiles during cancer progression. Studies of dietary phytochemicals on cancer signaling pathway regulation have been conducted to search for potent signaling regulatory agents. The present study was designed to evaluate any suppressive effect of maslinic acid on PKC expression in human B-lymphoblastoid cells (Raji cells), and to identify the PKC isoforms expressed. Effects of maslinic acid on PKC activity were determined using a PepTag assay for non-radioactive detection of PKC. The highest expression in Raji cells was obtained at 20 nM PMA induced for 6 hours. Suppressive effects of maslinic acid were compared with those of four PKC inhibitors (H- 7, rottlerin, sphingosine, staurosporine) and two triterpenes (oleanolic acid and ursolic acid). The IC50 values achieved for maslinic acid, staurosporine, H-7, sphingosine, rottlerin, ursolic acid and oleanolic acid were 11.52, 0.011, 0.767, 2.45, 5.46, 27.93 and 39.29 uM, respectively. Four PKC isoforms, PKC beta I, beta II, delta, and zeta were identified in Raji cells via western blotting. Maslinic acid suppressed the expression of PKC beta I, delta, and zeta in a concentration-dependent manner. These preliminary results suggest promising suppressive effects of maslinic acid on PKC activity in Raji cells. Maslinic acid could be a potent cancer chemopreventive agent that may be involved in regulating many downstream signaling pathways that are activated through PKC receptors.|/ALTERNATIVE and IN VITRO TESTS/Tumor necrosis factor alpha (TNFalpha) has been used to treat certain tumors in clinic/al/ trials. However, the curative effect of TNFalpha has been undermined by the induced-NF-kappa B activation in many types of tumor. Maslinic acid (MA), a pharmacological/ly/ safe natural product, has been known for its important effects as anti-oxidant, anti-inflammatory, and anti-viral activities. The aim of this study was to determine whether MA potentiates the anti-tumor activity of TNFalpha though the regulation of NF-kappaB activation. /This study demonstrates/ that MA significantly enhanced TNFalpha-induced inhibition of pancreatic cancer cell proliferation, invasion, and potentiated TNFalpha-induced cell apoptosis by suppressing TNFalpha-induced NF-kappa B activation in a dose- and time-dependent manner. Addition of MA inhibited TNFalpha-induced I kappa B alpha degradation, p65 phosphorylation, and nuclear translocation. Furthermore, MA decreased the expression levels of NF-kappa B-regulated genes, including genes involved in tumor cell proliferation (Cyclin D1, COX-2 and c-Myc), apoptosis (Survivin, Bcl-2, Bcl-xl, XIAP, IAP-1), invasion (MMP-9 and ICAM-1), and angiogenesis (VEGF). In athymic nu/nu mouse model, we further demonstrated that MA significantly suppressed pancreatic tumor growth, induced tumor apoptosis, and inhibited NF-kappa B-regulated anti-apoptotic gene expression, such as Survivin and Bcl-xl. ...data demonstrate that MA can potentiate the anti-tumor activities of TNFalpha and inhibit pancreatic tumor growth and invasion by activating caspase-dependent apoptotic pathway and by suppressing NF-kappa B activation and its downstream gene expression...|/ALTERNATIVE and IN VITRO TESTS/ Bioactivity-guided fractionation of apple peels was used to determine the chemical identity of bioactive constituents. Thirteen triterpenoids were isolated, and their chemical structures were identified. Antiproliferative activities of the triterpenoids against human HepG2 liver cancer cells, MCF-7 breast cancer cells, and Caco-2 colon cancer cells were evaluated. Most of the triterpenoids showed high potential anticancer activities against the three human cancer cell lines... All triterpenoids tested showed antiproliferative activity against Caco-2 cancer cells, especially 2alpha-hydroxyursolic acid, maslinic acid, 2alpha-hydroxy-3beta-{[(2E)-3-phenyl-1-oxo-2-propenyl]oxy}olean-12-en-28-oic acid, and 3beta-trans-p-coumaroyloxy-2alpha-hydroxyolean-12-en-28-oic acid, which displayed much higher antiproliferative activities...|For more Human Toxicity Excerpts (Complete) data for Maslinic Acid (8 total), please visit the HSDB record page.

bredemolic acid

... Interest for maslinic acid has increased because of its beneficial effects on health, which include antitumoral, antidiabetic, and antioxidant activities. Moreover, it has been attributed to anti-HIV and antiparasitic effects as well as vasorelaxant and stimulant of growth and protein-turnover properties.|Malinic acid is available as a dietary supplement as being a strong antioxidant and natural anti-inflammatory; available in consumer products such as olive oil, high protein fiber bars and skin care lotion products

A simple GC-MS method for the simultaneous determination of betulinic, corosolic, maslinic, oleanolic and ursolic acids was developed.|Triterpenic acids, such as maslinic acid and oleanolic acid, are commonly found in olive fruits and have been associated with many health benefits. The drying and extraction methods, as well as the solvents used, are critical factors in the determination of their concentration in plant tissues. Thus, there is an emerging need for standardization of an efficient extraction protocol that determines triterpenic acid content in olive fruits. To evaluate common extraction methods of triterpenic acids from olive fruits and to determine the effect of the drying method on their content in order to propose an optimum protocol for their quantification. The efficacy of different drying and extraction methods was evaluated through the quantification of maslinic acid and oleanolic acid contents using the reversed-phase HPLC technique. Data showed that ultrasonic assisted extraction with ethanol or a mixture of ethanol:methanol (1:1, v/v) resulted in the recovery of significantly higher amounts of triterpenic acids than other methods used. The drying method also affected the estimated triterpenic acid content; frozen or lyophilized olive fruit material gave higher yields of triterpenic acids compared with air-dried material at both 35 degrees C and 105degrees C...|A liquid chromatography-mass spectrometry method was developed and validated for the quantitative determination of seven triterpenoids, 3-beta-O-alpha-L-arabinopyranosylsiaresinolic acid-28-O-beta-D-glucopyranosyl ester, ziyuglycoside I, pomolic acid, maslinic acid, colosic acid, oleanolic acid and ursolic acid in Pyrola decorata H. Andres. Chromatographic separation was achieved on a Hypersil C18 column using isocratic elution followed by a linear gradient elution of methanol and water as mobile phase. The analytes were ionized by atmospheric pressure chemical ionization source and determined on selected ion monitoring mode. All analytes showed good linearity (r2 > or = 0.9984) within the test ranges and the recovery rates were 94.5% - 103.3%. Satisfactory precision and reproducibility were obtained with relative standard deviation less than 5%. The method was simple, accurate and performed well in application to the determination of twenty commercial samples of P. decorata collected from different regions of China. It could be used for the quality control of both plant materials and preparations of P. decorata.

Maslinic acid, a pentacyclic triterpene from olives, has been reported to exert beneficial effects on health, including anticarcinogenic activity. Despite its importance, little is known about its bioavailability in both humans and animals. A fundamental step for this evaluation consisted of measuring this compound in blood. Therefore, a simple high-performance liquid chromatography (HPLC) method with diode array detection has been developed. Maslinic acid contained in plasma was extracted twice using ethyl acetate. After centrifugation, the organic fraction was evaporated to dryness and the residue was reconstituted with methanol/water (75:25, v/v) and analyzed by HPLC. The method was validated by obtaining a linear correlation (r2 = 0.999) and an average recovery of 99%. Precision expressed as the coefficient of variation ranged from 1.23 to 9.06%. The oral administration of maslinic acid (50 mg/kg) to rats and its subsequent detection in plasma showed that the method is suitable for absorption, distribution, and metabolism studies.

Lipids -> Prenol Lipids [PR] -> Isoprenoids [PR01] -> C30 isoprenoids (triterpenes) [PR0106]