Maslinic acid

ChemicalBook > CAS DataBase List > Maslinic acid

Product Name: Maslinic acid
CAS No.: 4373-41-5
Chemical Name: Maslinic acid
Synonyms: CRATEGOLIC ACID;Crataegolic acid;MasL;maslinicaci;Masalic acid;Hawthorn acid;Maslinic acid-RM;MASLINIC ACID, 98%;Maslinic acid (6CI);Masalic Acid Powder
CBNumber: CB3345863
Molecular Formula: C30H48O4
Formula Weight: 472.7
MOL File: 4373-41-5.mol

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Maslinic acid Property

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)

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Safety

Safety Statements: 24/25
WGK Germany: 3
HS Code: 29181990
Hazardous Substances Data: 4373-41-5(Hazardous Substances Data)

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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: M6699
Product name: Maslinic acid
Purity: ≥98% (HPLC)
Packaging: 5mg
Price: $216
Updated: 2024/03/01

Sigma-Aldrich

Product number: 68594
Product name: Maslinic acid
Purity: analytical standard
Packaging: 5mg
Price: $459
Updated: 2022/05/15

Cayman Chemical

Product number: 10009645
Product name: Maslinic Acid
Purity: >98%
Packaging: 1mg
Price: $31
Updated: 2024/03/01

Cayman Chemical

Product number: 10009645
Product name: Maslinic Acid
Purity: >98%
Packaging: 5mg
Price: $105
Updated: 2024/03/01

Sigma-Aldrich

Product number: M6699
Product name: Maslinic acid
Purity: ≥98% (HPLC)
Packaging: 25mg
Price: $556.8
Updated: 2024/03/01

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Maslinic acid Chemical Properties,Usage,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 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.

Uses

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

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.

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View Lastest Price from Maslinic acid manufacturers

Shaanxi Cuikang Pharmaceutical Technology Co., Ltd

Product: Maslinic acid 4373-41-5
Price: US $0.00/g
Min. Order: 1g
Purity: HPLC≥98%
Supply Ability: 100kg
Release date: 2024-03-14

Hebei Zhuanglai Chemical Trading Co Ltd

Product: Masalic Acid Powder 4373-41-5
Price: US $150.00/kg
Min. Order: 1kg
Purity: 99%
Supply Ability: 500kg
Release date: 2024-11-18

Chongqing Zhihe Biopharmaceutical Co., Ltd.

Product: Maslinic acid 4373-41-5
Price: US $0.00-0.00/kg
Min. Order: 0.10000000149011612kg
Purity: 10%-30% and 》98%
Supply Ability: 20tons
Release date: 2024-01-04

4373-41-5, Maslinic acidRelated Search:

4-Hydroxycinnamic acid Stearic acid 1,7-DIOXASPIRO[5.5]UNDECANE Citric acid Folic acid Ethyl 2-(Chlorosulfonyl)acetate Oleanolic acid Ascoric Acid Methyl maslinate Arjunolic acid (2α,3β)-2,3-Dihydroxy-olean-12-en-28-oic acid ethyl ester Maslinic acid (2α,3β)-2,3-Dihydroxy-olean-12-en-28-oic acid 2-hydroxyethyl ester, (2α,3β)- 2,3-Bis(acetyloxy)-olean- 12-en-28-oic acid 2,3-BIS(ACETYLOXY)-(2ALPHA,3BETA)-OLEAN-12-EN-28-OIC ACID METHYL ESTER (2α,3β)-2,3-Dihydroxy-olean-12-en-28-oic acid carboxymethyl ester 2-ACETYLOXY-3-HYDROXY-(2ALPHA,3BETA)-OLEAN-12-EN-28-OIC ACID METHYL ESTER (2α,3β)- 2-(Acetyloxy)-3-hydroxy- olean-12-en-28-oic acid

CRATEGOLIC ACID

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

Crataegolic acid

Crategolic acid, froM Crataegus pinnatifida

Olean-12-en-28-oicacid, 2,3-dihydroxy-, (2a,3b)-

MASLINIC ACID FROM CRATAEGUS PINNATI

Crategolic acid, 98%, from Crataegus pinnatifida Bunge

Maslinic acid (2alpha,3beta)-2,3-Dihydroxy-olean-12-en-28-oic acid

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

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

Maslinic acid-RM

Masalic Acid Powder

4373-41-5

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