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Maslinic acid

CAS No.
4373-41-5
Chemical Name:
Maslinic acid
Synonyms
CRATEGOLIC ACID;Crataegolic acid;MasL;maslinicaci;Masalic acid;Hawthorn acid;MASLINIC ACID, 98%;Maslinic acid (6CI);Maslinic acid 10-98%;Maslinic acid 4373-41-5
CBNumber:
CB3345863
Molecular Formula:
C30H48O4
Molecular Weight:
472.7
MDL Number:
MFCD00049293
MOL File:
4373-41-5.mol
MSDS File:
SDS
Last updated:2024-03-14 18:28:40

Maslinic acid Properties

Melting point 267~269℃
Boiling point 570.0±50.0 °C(Predicted)
Density 1.14±0.1 g/cm3(Predicted)
storage temp. 2-8°C
solubility acetone: soluble1mg/mL, clear, colorless
pka 4.63±0.70(Predicted)
form powder
color white to off-white
Stability Hygroscopic
InChIKey MDZKJHQSJHYOHJ-LLICELPBSA-N
SMILES [C@@]12(C)CC[C@@]3([H])C(C)(C)[C@@H](O)[C@H](O)C[C@]3(C)[C@@]1([H])CC=C1[C@]3([H])CC(CC[C@]3(C(=O)O)CC[C@@]21C)(C)C |&1:0,4,9,11,14,16,21,27,33,r|
LogP 7.870 (est)
FDA UNII E233J88OHQ

SAFETY

Risk and Safety Statements

Safety Statements  24/25
WGK Germany  3
HS Code  29181990

Maslinic acid price More Price(30)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich M6699 Maslinic acid ≥98% (HPLC) 4373-41-5 5mg $216 2024-03-01 Buy
Sigma-Aldrich 68594 Maslinic acid analytical standard 4373-41-5 5mg $459 2022-05-15 Buy
Cayman Chemical 10009645 Maslinic Acid >98% 4373-41-5 1mg $31 2024-03-01 Buy
Cayman Chemical 10009645 Maslinic Acid >98% 4373-41-5 5mg $105 2024-03-01 Buy
Sigma-Aldrich M6699 Maslinic acid ≥98% (HPLC) 4373-41-5 25mg $556.8 2024-03-01 Buy
Product number Packaging Price Buy
M6699 5mg $216 Buy
68594 5mg $459 Buy
10009645 1mg $31 Buy
10009645 5mg $105 Buy
M6699 25mg $556.8 Buy

Maslinic acid Chemical Properties,Uses,Production

Description

Maslinic acid (2-α,3-β-dihydroxyolean-12-en-28-oic acid) is a pentacyclic triterpene abundant in the cuticular lipid layer of olive fruits (Bianchi et al.,1994) .It is a compound of 30 carbon atoms grouped in five cycles that have several substitutes. Maslinic acid presents two hydroxyl groups bound to carbons 2 and 3,one carboxyl group bound to carbon 17, and a double bond between carbons 12 and 13.It is a highly hydrophobic compound of low water solubility. Maslinic acid is synthesized in plants via the cytoplasmic acetate/mevalonate pathway that leads to oxidosqualene (Seo et al., 1988).Oxidosqualene is cycled by various oxidosqualene cyclases, among them β-amyrin synthase, which catalyzes the transformation of oxydosqualene into β-amyrin (olean-12-3n-3β-ol). Afterwards,β-amyrin is converted by successive reactions into erythrodiol, oleanolic acid, and finally maslinic acid (Saimaru et al.,2007; Stiti et al.,2007).

Description

Maslinic acid is found in a number of natural sources, most notably pomace olive oil (orujo). This pentacyclic triterpene has an antiproliferative effect against Caco-2 cancer cells (EC50 = 15 μM), HT-29 human colon cancer cells (EC50 = 74 μM), 1321N1 astrocytoma cells (IC50 = 25 μM), and human leukemia (CCRF-CEM and CEM/ADR5000) cells (IC50 = 7 μM and 9 μM respectively). Maslinic acid''s antiproliferative activity likely comes from the induction of an oxidative apoptotic pathway, causing cell cycle and cytoskeleton alterations. Maslinic acid has been found to attenuate intracellular oxidative stress via inhibition of NO and H2O2 production and reduction of pro-inflammatory cytokine generation in murine macrophages. Recently maslinic acid has been found to inhibit the spread of the HIV virus by inhibiting the replication of a primary HIV-1 isolate as well as decreased the cytopathic effect and p24 antigen levels in MT2 cells.

Uses

Maslinic Acid is an apoptosis inducer in lung cancer cells, occuring under normoxic and hypoxic conditions.

Uses

Maslinic acid may be used as an analytical reference standard for the quantification of the analyte in the leaves of Ziziphus species and fruits using different chromatography techniques.

Definition

Maslinic acid is a pentacyclic triterpenoid that is olean-12-ene substituted by hydroxy groups at positions 2 and 3 and a carboxy group at position 28 (the 2alpha,3beta stereoisomer). It is isolated from Olea europaea and Salvia canariensis and exhibits anti-inflammatory, antioxidant and antineoplastic activity. It has a role as an antioxidant, an antineoplastic agent, an anti-inflammatory agent and a plant metabolite. It is a pentacyclic triterpenoid and a dihydroxy monocarboxylic acid. It derives from a hydride of an oleanane.

General Description

Maslinic acid belongs to the class of triterpenic acids, a group of phytochemicals present in a large variety of plants. It exhibits a broad-spectrum of biological properties such as cardiovascular, antihyperlipidemic, antioxidant effects, hepatoprotective effects, antitumor activity. It is also involved in enhancing the cellular immune system.

Biological Activity

Maslinic acid is found in a number of natural sources, most notably pomace olive oil (orujo). This pentacyclic triterpene has an antiproliferative effect against Caco-2 cancer cells (EC50 = 15 μM), HT-29 human colon cancer cells (EC50 = 74 μM), 1321N1 astrocytoma cells (IC50 = 25 μM), and human leukemia (CCRF-CEM and CEM/ADR5000) cells (IC50 = 7 μM and 9 μM respectively). Maslinic acid's antiproliferative activity likely comes from the induction of an oxidative apoptotic pathway, causing cell cycle and cytoskeleton alterations. Maslinic acid has been found to attenuate intracellular oxidative stress via inhibition of NO and H2O2 production and reduction of pro-inflammatory cytokine generation in murine macrophages. Recently maslinic acid has been found to inhibit the spread of the HIV virus by inhibiting the replication of a primary HIV-1 isolate as well as decreased the cytopathic effect and p24 antigen levels in MT2 cells.

Biochem/physiol Actions

Predominant triterpenoid found in olives. Anti-proliferative. Promising chemopreventive agent.

Cytotoxicity

IC50 (μg/mL): 6.48 (518A2), 13.61(HT29),17.58 (MCF-7), 11.06 (A549), 9.22(A2780), 8.04 (8505C) (Siewert et al.2014)
IC50 (μg/mL): 9.97 (NIH-3T3)(Sommerwerk et al. 2016).

References

[1] reyes-zurita f j, rufino-palomares e e, lupiáez j a, et al. maslinic acid, a natural triterpene from olea europaea l., induces apoptosis in ht29 human colon-cancer cells via the mitochondrial apoptotic pathway[j]. cancer letters, 2009, 273(1): 44-54.
[2] garcía, a. compound from olive-pomace oil inhibits hiv spread. 070709111536, 1-1 (2007).
[3] liu j, sun h, duan w, et al. maslinic acid reduces blood glucose in kk-ay mice[j]. biological and pharmaceutical bulletin, 2007, 30(11): 2075-2078.
[4] guan t, qian y, tang x, et al. maslinic acid, a natural inhibitor of glycogen phosphorylase, reduces cerebral ischemic injury in hyperglycemic rats by glt‐1 up‐regulation[j]. journal of neuroscience research, 2011, 89(11): 1829-1839.

Maslinic acid Preparation Products And Raw materials

Raw materials

Preparation Products

Global( 251)Suppliers
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View Lastest Price from Maslinic acid manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Maslinic acid pictures 2024-03-27 Maslinic acid
4373-41-5
US $0.00-0.00 / kg 0.10000000149011612kg 10%-30% and 》98% 20tons Chongqing Zhihe Biopharmaceutical Co., Ltd.
Maslinic acid pictures 2024-03-27 Maslinic acid
4373-41-5
US $0.00 / g 1g HPLC≥98% 100kg Shaanxi Cuikang Pharmaceutical Technology Co., Ltd
Maslinic acid pictures 2023-11-08 Maslinic acid
4373-41-5
US $0.00 / kg 1kg 98% 2000ton Shaanxi Haibo Biotechnology Co., Ltd
  • Maslinic acid pictures
  • Maslinic acid
    4373-41-5
  • US $0.00-0.00 / kg
  • 10%-30% and 》98%
  • Chongqing Zhihe Biopharmaceutical Co., Ltd.
  • Maslinic acid pictures
  • Maslinic acid
    4373-41-5
  • US $0.00 / g
  • HPLC≥98%
  • Shaanxi Cuikang Pharmaceutical Technology Co., Ltd
  • Maslinic acid pictures
  • Maslinic acid
    4373-41-5
  • US $0.00 / kg
  • 98%
  • Shaanxi Haibo Biotechnology Co., Ltd
MASLINIC ACID, 98% (4aS,6aR,6aS,6bR,8aR,10R,11R,12aR,14bS)-10,11-dihydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid CRATEGOLIC ACID (PLEASE CALL) (2alpha,3beta)-2,3-Dihydroxy-olean-12-en-28-oic acid CRATEGOLIC ACID(MASLINIC ACID)(P) Maslinic Acid(Crategolic Acid) Maslinic acid, Crataegolic acid Crategolic acid, froM Crataegus pinnatifida Olean-12-en-28-oicacid, 2,3-dihydroxy-, (2a,3b)- MASLINIC ACID FROM CRATAEGUS PINNATI Maslinic acid (2alpha,3beta)-2,3-Dihydroxy-olean-12-en-28-oic acid Crategolic acid, 98%, from Crataegus pinnatifida Bunge Keywords Lagerstroemia speciosa extract Keywords loquat leaf extract Maslinic acid 4373-41-5 10,11-dihydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid maslinic acid, HPLC≥98% Maslinic acid 10-98% 2α-Hydroxyoleanoic Acid MasL maslinicaci hot selling maslinic acid Tianfu Chem 4373-41-5 Maslinic acid CRATEGOLIC ACID Crataegolic acid 2α-Hydroxyoleanoic Acid 2α-Hydroxyoleanolic acid Maslinic acid (6CI) inhibit,Nuclear factor-κB,Human immunodeficiency virus,HIV,Maslinic acid,Nuclear factor-kappaB,NF-κB,Inhibitor,Bacterial (4aS,6aS,6bR,8aR,10R,11R,12aR,12bR,14bS)-10,11-Dihydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid Olean-12-en-28-oic acid, 2,3-dihydroxy-, (2α,3β)- Hawthorn acid Masalic acid 4373-41-5 Miscellaneous Pentacyclic Triterpenes Natural Products