101821-23-2

Basic information

• Product Name: 15-Hydroxyabieta-7,13-dien-18-oic acid
• Synonyms: 15-Hydroxyabieta-7,13-dien-18-oic acid;15-Hydroxyabietic acid
• CAS NO: 101821-23-2
• Molecular Formula: C20H30O3
• Molecular Weight: 318.45
• Product Categories: chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
• Mol File: 101821-23-2.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 15-Hydroxyabieta-7,13-dien-18-oic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 15-Hydroxyabieta-7,13-dien-18-oic acid(101821-23-2)
• EPA Substance Registry System: 15-Hydroxyabieta-7,13-dien-18-oic acid(101821-23-2)

Safety Data

• Hazardous Substances Data: 101821-23-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
15-Hydroxyabieta-7,13-dien-18-oic acid is used as an anti-inflammatory agent for its ability to reduce inflammation, which can be beneficial in treating a variety of inflammatory conditions.
Used in Oncology:
In the field of oncology, 15-Hydroxyabieta-7,13-dien-18-oic acid is utilized as an anti-tumor agent due to its potential to inhibit tumor growth and progression, making it a candidate for cancer treatment.
Used in Neurodegenerative Disease Treatment:
15-Hydroxyabieta-7,13-dien-18-oic acid is employed as a therapeutic agent for neurodegenerative diseases, leveraging its potential to protect and restore neuronal function, thereby slowing disease progression.
Used in Immunomodulation:
15-Hydroxyabieta-7,13-dien-18-oic acid is used as an immunomodulatory agent to regulate the immune response, which can be advantageous in managing autoimmune diseases and conditions requiring immune system modulation.
Overall, 15-Hydroxyabieta-7,13-dien-18-oic acid's multifaceted applications across different medical fields highlight its potential as a versatile therapeutic agent, with ongoing research aimed at unlocking its full potential.

Upstream product

• 67-64-1 acetone 
• 388120-49-8 7-bromo-1,4a-dimethyl-1,2,3,4,4a,4b,5,6,10,10a-decahydro-phenanthrene-1-carboxylic acid 
• 20085-81-8 13-Oxopodocarp-8⁽¹⁴⁾-en-18-saeure-methylester 
• 5708-85-0 13-oxo-13-deisopropyl-abiet-8⁽¹⁴⁾en-15-oic acid 
• 105405-29-6 methyl 13-oxo-podocarp-8-en-18-oate 
• 113903-96-1 7-(1-hydroperoxy-1-methyl-ethyl)-1,4a-dimethyl-1,2,3,4,4a,4b,5,6,10,10a-decahydro-phenanthrene-1-carboxylic acid 
• 514-10-3 abietic acid 
• 388120-50-1 C₂₁H₃₂O₃ 
• 19402-34-7 methyl abieta-8,13⁽¹⁵⁾-dien-18-oate 

Downstream Products

• 113903-96-1 7-(1-hydroperoxy-1-methyl-ethyl)-1,4a-dimethyl-1,2,3,4,4a,4b,5,6,10,10a-decahydro-phenanthrene-1-carboxylic acid 

Relevant articles and documents

Resin Acid Conversion with CYP105A1: An Enzyme with Potential for the Production of Pharmaceutically Relevant Diterpenoids

Cytochrome P450s are very versatile enzymes with great potential for biotechnological applications because of their ability to oxidize unactivated C-H bonds. CYP105A1 from Streptomyces griseolus was first described as a herbicide-inducible sulfonylurea hydroxylase, but it is also able to convert other substrates such as vitamin D3. To extend the substrate pool of this interesting enzyme further, we screened a small diterpenoid compound library and were able to show the conversion of several resin acids. Binding of abietic acid, dehydroabietic acid, and isopimaric acid to the active site was assayed, and Vmax and Km values were calculated. The products were analyzed by NMR spectroscopy and identified as 15-hydroxyabietic acid, 15-hydroxydehydroabietic acid, and 15,16-epoxyisopimaric acid. As the observed products are difficult to obtain by chemical synthesis, CYP105A1 has proved to be a promising candidate for biotechnological applications that combine bioconversion and chemical synthesis to obtain functionalized resin acids.

Identification of radical species derived from allergenic 15-hydroperoxyabietic acid and insights into the behaviour of cyclic tertiary allylic hydroperoxides in Fe(II)/Fe(III) systems

To understand the skin sensitization mechanism of 15-hydroperoxyabietic acid, the major allergen in colophony, we first examined the formation of potential reactive radicals derived from its reaction with light, heat and TPP-Fe3+. Trapping with 1,1,3,3-tetramethylisoindolin-2-yloxyl nitroxide confirmed the?formation of carbon-centred radicals derived from allyloxyl/allylperoxyl radicals as a consequence of the hydroperoxide scission. Particular interest was further given to the reactivity with Fe(II)/Fe(III) due to?the biological importance of haem containing enzymes. Using a monocyclic 15-hydroperoxyabietic acid-like compound as a model of allergenic allylic hydroperoxides, we evidenced, by the ESR spin-trapping technique, the competition between carbon and oxygen-centred radicals formed in the presence of Fe(II)/Fe(III) in organic/aqueous media. We complemented the study by showing the possibility of formation, via a radical mechanism induced by ferric chloride, of an adduct between the allylic hydroperoxide and N-acetyl-cysteine ethyl ester. The results gave new knowledge on the possible generation of highly reactive radicals that could lead to the formation of antigenic structures.

Conversion of a cyclic α,β-unsaturated ketone into a tertiary dienyl hydroperoxide: Application to the first hemisynthesis of 15-hydroperoxyabietic acid

The first hemisynthesis of 15-hydroperoxyabietic acid, a major contact allergen among the oxidation products of colophony, is reported. The key step includes a new approach to easily obtain a dienyl tertiary hydroperoxide from a cyclic α,β-unsaturated ketone. The procedure is based on the formation of a bromodiene using a Vilsmeier's reagent, followed by a halogen/metal exchange and alkylation with acetone, to afford the dienyl alcohol precursor of the hydroperoxide.