Cas no 79-54-9 (Levopimaric Acid)

Levopimaric Acid is a diterpenoid resin acid derived primarily from pine rosin. It is characterized by its conjugated double-bond system and carboxylic acid functionality, which make it a versatile intermediate in organic synthesis and industrial applications. Key advantages include its role as a precursor for high-value derivatives, such as hydrogenated resins and specialty chemicals, due to its reactive sites. Its natural origin and biodegradability also align with sustainable chemistry practices. Levopimaric Acid exhibits stability under standard conditions and is utilized in adhesives, coatings, and ink formulations, where it enhances performance through improved tack and adhesion properties. Its structural features further enable modifications for tailored chemical applications.
Levopimaric Acid structure
Levopimaric Acid structure
Product Name:Levopimaric Acid
CAS No:79-54-9
MF:C20H30O2
MW:302.451006412506
CID:565401
PubChem ID:221062
Update Time:2025-10-28

Levopimaric Acid Chemical and Physical Properties

Names and Identifiers

    • 1-Phenanthrenecarboxylicacid, 1,2,3,4,4a,4b,5,9,10,10a-decahydro-1,4a-dimethyl-7-(1-methylethyl)-,(1R,4aR,4bS,10aR)-
    • Levopimaric Acid
    • (1R,4aR,4bS,10aR)-1,4a-dimethyl-7-propan-2-yl-2,3,4,4b,5,9,10,10a-octahydrophenanthrene-1-carboxylic acid
    • (1R,4aS,4bR)-1,4a-dimethyl-7-propan-2-yl-2,3,4,4b,5,9,10,10a-octahydro phenanthrene-1-carboxylic acid
    • Levopimaric acidneat
    • 8(14),12-Abietadien-18-oic acid
    • abieta-8(14),12-dien-18-oic acid
    • Abieta-8(14),12-dien-18-saeure
    • Abietadien-8(14).12-saeure-(18)
    • AC1Q1OIE
    • A-pimaric acid
    • B-Pimaric Acid
    • Laevopimarsaeure
    • l-Pimaric acid
    • l-Sapietic acid
    • NSC4827
    • CS-0128313
    • 1-Phenanthrenecarboxylic acid, 1,2,3,4,4a,4b,5,9,10,10a-decahydro-1,4a-dimethyl-7-(1-methylethyl)-, (1theta-(1alpha,4abeta,4balpha,10aalpha))-
    • 1-Phenanthrenecarboxylic acid, 1,2,3,4,4a,4b,5,9,10,10a-decahydro-1,4a-dimethyl-7-(1-methylethyl)-, (1R-(1alpha,4abeta, 4balpha,10aalpha))-
    • .DELTA.6,8(14)-Abietadienoic acid
    • .beta.-Pimaric acid
    • 13-isopropylpodocarpa-8(14),12-dien-15-oic acid
    • UNII-6073C2A77I
    • beta-Pimaric acid
    • Q6535822
    • LEVOPIMARIC ACID [MI]
    • DTXSID20878526
    • 1-Phenanthrenecarboxylic acid,2,3,4,4a,4b,5,9,10,10a-decahydro-1,4a-dimethyl-7-(1-methylethyl)-, [1R-(1.alpha.,4a.beta.,4b.alpha.,10a.alpha.)]-
    • Podocarpa-8(14), 13-isopropyl-
    • RWWVEQKPFPXLGL-ONCXSQPRSA-N
    • NSC-4827
    • HY-N7431
    • AKOS032946285
    • 1-PHENANTHRENECARBOXYLIC ACID, 1,2,3,4,4A,4B,5,9,10,10A-DECAHYDRO-1,4A-DIMETHYL-7-(1-METHYLETHYL)-, (1R,4AR,4BS,10AR)-
    • CHEBI:29615
    • (1R,4aR,4bS,10aR)-7-isopropyl-1,4a-dimethyl-2,3,4,4b,5,9,10,10a-octahydrophenanthrene-1-carboxylic acid
    • (-)-LEVOPIMARIC ACID
    • Podocarpa-8(14),12-dien-15-oic acid, 13-isopropyl-
    • delta6,8(14)-Abietadienoic acid
    • SCHEMBL152258
    • 79-54-9
    • 6073C2A77I
    • NSC 4827
    • L-Pimarate
    • Levopimarate
    • 1-Phenanthrenecarboxylic acid, 1,2,3,4,4a,4b,5,9,10,10a-decahydro-1,4a-dimethyl-7-(1-methylethyl)-, (1R-(1alpha,4abeta,4balpha,10aalpha))-
    • 1-Phenanthrenecarboxylic acid, 1,2,3,4,4a,4b,5,9,10,10a-decahydro-1,4a-dimethyl-7-(1-methylethyl)-, (1R-(1.alpha.,4a.beta.,4b.alpha.,10a.alpha.))-
    • DA-54883
    • DTXCID201016571
    • I2-Pimaric acid
    • Podocarpa-8(14),12-dien-15-oic acid, 13-isopropyl-(8CI)
    • Inchi: 1S/C20H30O2/c1-13(2)14-6-8-16-15(12-14)7-9-17-19(16,3)10-5-11-20(17,4)18(21)22/h6,12-13,16-17H,5,7-11H2,1-4H3,(H,21,22)/t16-,17+,19+,20+/m0/s1
    • InChI Key: RWWVEQKPFPXLGL-ONCXSQPRSA-N
    • SMILES: OC([C@]1(C)CCC[C@]2(C)[C@H]3CC=C(C(C)C)C=C3CC[C@H]21)=O

Computed Properties

  • Exact Mass: 302.2247
  • Monoisotopic Mass: 302.225
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 22
  • Rotatable Bond Count: 2
  • Complexity: 542
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 4
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 4.8
  • Topological Polar Surface Area: 37.3?2

Experimental Properties

  • Density: 1.0434 (rough estimate)
  • Melting Point: 150°
  • Boiling Point: 383.47°C (rough estimate)
  • Flash Point: 204.6°C
  • Refractive Index: 1.4800 (estimate)
  • PSA: 37.3
  • LogP: 5.20620
  • Specific Rotation: D20 -280.4° (c = 0.7 in alcohol); D14 -266.6° (c = 0.4 in chloroform)

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Additional information on Levopimaric Acid

Levopimaric Acid (CAS No. 79-54-9): A Comprehensive Overview

Levopimaric Acid (CAS No. 79-54-9) is a naturally occurring diterpenoid acid that has garnered significant attention in the fields of chemistry, biology, and pharmacology due to its diverse biological activities and potential therapeutic applications. This compound is primarily derived from the resin of coniferous trees, particularly those belonging to the genus Picea. Its unique chemical structure and biological properties make it a valuable subject of research and development in various scientific disciplines.

The chemical structure of Levopimaric Acid is characterized by a tricyclic diterpenoid skeleton with a carboxylic acid functional group. This structure confers the compound with a range of biological activities, including anti-inflammatory, antimicrobial, and anticancer properties. Recent studies have further elucidated the mechanisms by which Levopimaric Acid exerts these effects, providing a deeper understanding of its potential therapeutic applications.

In the realm of anti-inflammatory research, Levopimaric Acid has shown promising results in reducing inflammation in both in vitro and in vivo models. Studies have demonstrated that it can inhibit the production of pro-inflammatory cytokines such as TNF-α and IL-6, as well as reduce the expression of cyclooxygenase-2 (COX-2), a key enzyme involved in the inflammatory response. These findings suggest that Levopimaric Acid could be a potential candidate for the development of novel anti-inflammatory drugs.

Beyond its anti-inflammatory properties, Levopimaric Acid has also been investigated for its antimicrobial activity. Research has shown that it exhibits broad-spectrum antimicrobial activity against various bacterial and fungal pathogens. This activity is attributed to its ability to disrupt microbial cell membranes and inhibit essential metabolic pathways. The antimicrobial potential of Levopimaric Acid makes it an attractive candidate for the development of new antimicrobial agents, particularly in light of the growing global threat of antibiotic resistance.

In the field of oncology, Levopimaric Acid has demonstrated significant anticancer activity against various types of cancer cells. Studies have shown that it can induce apoptosis (programmed cell death) in cancer cells by modulating key signaling pathways such as p53 and Bcl-2. Additionally, Levopimaric Acid has been found to inhibit angiogenesis, the process by which new blood vessels form to supply nutrients to tumors, thereby limiting tumor growth and metastasis. These findings highlight the potential of Levopimaric Acid as a novel anticancer agent.

The pharmacological properties of Levopimaric Acid, including its bioavailability and metabolic stability, are also important considerations for its therapeutic development. Recent studies have explored various formulations and delivery systems to enhance the bioavailability and efficacy of Levopimaric Acid. For example, nanoparticle-based delivery systems have shown promise in improving the solubility and stability of the compound, thereby enhancing its therapeutic potential.

In addition to its direct biological activities, Levopimaric Acid has also been studied for its potential as a lead compound for drug discovery. Its unique chemical structure provides a valuable scaffold for the design and synthesis of novel compounds with enhanced biological activities. Researchers are actively exploring structural modifications and derivatization strategies to optimize the pharmacological properties of Levopimaric Acid.

The environmental impact of Levopimaric Acid is another area of interest. As a naturally occurring compound derived from renewable resources, it offers an environmentally friendly alternative to synthetic chemicals. Sustainable extraction methods and biotechnological approaches are being developed to ensure the responsible production and use of Levopimaric Acid.

In conclusion, Levopimaric Acid (CAS No. 79-54-9) is a multifaceted compound with significant potential in various fields of research and application. Its anti-inflammatory, antimicrobial, and anticancer properties make it a valuable candidate for the development of novel therapeutic agents. Ongoing research continues to uncover new insights into its mechanisms of action and optimize its pharmacological properties, paving the way for future innovations in medicine and biotechnology.

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