20257-75-4

Usage

Uses

Used in Pharmaceutical Industry:
(E)-5-[(1R,4aβ)-Decahydro-5,5,8aα-trimethyl-2-methylenenaphthalene-1-yl]-3-methyl-2-pentenoic acid is used as a potential active pharmaceutical ingredient (API) for its possible biological activity, which may be harnessed to develop new drugs or therapeutic agents. (E)-5-[(1R,4aβ)-Decahydro-5,5,8aα-trimethyl-2-methylenenaphthalene-1-yl]-3-methyl-2-pentenoic acid's hydrophobic nature could play a role in its interaction with biological targets, such as receptors or enzymes.
Used in Perfume Industry:
In the perfume industry, (E)-5-[(1R,4aβ)-Decahydro-5,5,8aα-trimethyl-2-methylenenaphthalene-1-yl]-3-methyl-2-pentenoic acid is used as a potential ingredient for creating unique fragrances. Its complex molecular structure may contribute to novel olfactory properties, offering a distinct scent profile that could be valuable in the development of new perfumes or colognes.
Further research and development are required to explore the full potential of (E)-5-[(1R,4aβ)-Decahydro-5,5,8aα-trimethyl-2-methylenenaphthalene-1-yl]-3-methyl-2-pentenoic acid in these and other industries, as well as to optimize its synthesis and production methods for commercial applications.

Upstream product

• 10395-36-5 (+/-)-Labda-8(20),13-dien-15-oic acid 
• 10395-37-6 methyl ent-labda-8⁽¹⁷⁾,13-E-dien-15-oate, methyl copalate 
• 727723-06-0 2-((4aR,6aS,7R,10aS,10bR)-3,3,6a,10b-tetramethyl-8-methylenedecahydro-1H-naphtho[2,1-d][1,3]dioxin-7-yl)acetaldehyde 
• 1234554-78-9 3α-hydroxy-13-oxo-15,16-dinor-ent-labda-8(17)-ene 
• 142037-79-4 andrographolide 

Downstream Products

• 10395-37-6 methyl ent-labda-8⁽¹⁷⁾,13-E-dien-15-oate, methyl copalate 
• 191274-20-1 (E)-3-Methyl-5-((1R,4aR,8aR)-5,5,8a-trimethyl-2-methylene-decahydro-naphthalen-1-yl)-pent-2-enoic acid (S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester 

Relevant academic research and scientific papers

(13E)-(-)-labda-8(17),13-dien-15-oic acid

In the title compound, C20H32O2, the two six-membered rings have a 1C4 chair conformation and the rings are trans-fused. The crystal structure is stabilized by approximately symmetricR22(8)-type hydrogen bonds.

Bioassay guided identification of small chaperone proteins α-crystallin and Hsp27 inhibitors from Copaiba oil

Over-expression of small chaperone proteins in cancer tissue contributes to the resistance of chemotherapy. Targeting these small chaperones including α-crystallin and heat shock protein 27 (Hsp27) is a promising strategy for cancer treatment. Hardwickiic acid (HA), a clerodane diterpenoid from Copaiba oil has been reported to inhibit Hsp27. We expect to identify new small chaperone inhibitors from Copaiba oil that is abundant of diterpenoids. In the current study, cytotoxicity and anti-chaperone assay guided isolation of Copaiba oil led to two major fractions (non-acidic and acidic components) and seven sub-fractions from the acidic components. The non-acidic components and one sub-fraction showed significant cytotoxicity in prostate cancer cells. Four sub-fractions exhibited potent anti-chaperone activity. Three chemical components were identified from these sub-fractions including copalic acid, hardwickiic acid and 3-acetoxycopalic acid. All three compounds inhibited the chaperone activities of α-crystallin and Hsp27. In addition, these compounds enhanced the anti-proliferative activity of the chemotherapeutic agent carboplatin in LNCaP cells. 3-Acetoxycopalic acid slightly decreased the level of Hsp27 client protein signal transducer and activator of transcription 3 (Stat3) in PC3 cells. Overall, several diterpenoids were identified to be small chaperone inhibitors and could be used as lead compounds for the development of more potent derivatives.

Synthesis of (-)-agathic acid and (-)-copalic acid from andrographolide via a regioselective Barton-McCombie reaction

The first synthesis of the ent-labdane diterpenoid (-)-agathic acid (1) with antibacterial activity is described. A chiral pool approach was employed with a linear sequence of 14 steps starting from readily available and inexpensive andrographolide. The regioselective deoxygenation in terms of Barton-McCombie free radical reaction completed a key step in the synthesis. (-)-Copalic acid (2), an analogue of (-)-agathic acid, has been conveniently synthesized from the key intermediate 7 in five steps.

Synthetic studies on natural diterpenoid glyceryl esters

Synthesis of natural bicyclic and tricyclic diterpenoid diacylglycerols has been performed by regioselective coupling of terpenoid acid with glycerol at 1'-sn position. This method may be considered a general approach to obtain optically active acylglycerols. The preparation of 13C-labelled geranylgeranoic acid glyceryl esters is also described here. (C) 2000 Elsevier Science Ltd.