6730-83-2

Usage

Uses

Used in Pharmaceutical Industry:
Kaurenoic acid is used as an anticancer agent for its cytotoxic effects on multiple cancer cell lines, including prostate, colon, and breast cancer cells, with IC50 values ranging from 15.03 to 48.87 μg/ml.
Used in Antibacterial Applications:
Kaurenoic acid is used as an antibacterial agent, showing in vitro activity against S. epidermidis, S. capitis, E. faecalis, and S. haemolyticus with MICs ranging from 6.25 to 12.5 μg/ml.
Used in Anti-inflammatory Applications:
Kaurenoic acid is used as an anti-inflammatory agent, reducing colonic myeloperoxidase (MPO) activity and malondialdehyde (MDA) levels in a rat model of acetic acid-induced colitis, as well as colonic tissue damage, leukocytic infiltration, and submucosal edema when administered at a dose of 100 mg/kg.
Used in Biological Research:
Kaurenoic acid is used in biological studies for the kinetic profile of guaco syrup metabolites, such as coumarin, 7-hydroxycoumarin, o-coumaric acid, and kaurenoic acid, to identify alternative routes of coumarin metabolism in human plasma.

InChI:InChI=1/C20H30O2/c1-13-11-20-10-7-15-18(2,16(20)6-5-14(13)12-20)8-4-9-19(15,3)17(21)22/h14-16H,1,4-12H2,2-3H3,(H,21,22)/t14-,15-,16-,18+,19+,20+/m0/s1

Upstream product

• 150-96-9 3-hydroxy-3-methylpentanoic acid 
• 150-97-0 D,L-mevalonic acid 
• 469-85-2 kaurene 
• 10438-44-5 (-)-kaur-16-en-19-ol 
• 55102-94-8 C₂₀H₃₁IO₂ 
• 32940-15-1 5-methoxy-2-tetralone 
• 5572-83-8 (+/-)-13-Butylmercaptomethylen-14-oxo-5β.8α.9β.10α-podocarpan-19-saeuremethylester 
• 5095-25-0 (+/-)-14-Oxo-16ξ-hydroxy-17-nor-kauran-19-saeuremethylester 
• 5095-15-8 (+/-)-3-Oxo-14-methoxy-Δ^8,11,13-5β,10α-podocarpatrien-19-saeuremethylester 
• 5095-12-5 (+/-)-14-Methoxy-Δ^8.11.13-5β.10α-podocarpatrien-15-saeuremethylester 
• 5095-17-0 (+/-)-14-Hydroxy-Δ^8.11.13-5β.10α-podocarpatrien-15-saeure-methylester 
• 5095-16-9 (+/-)-14-Hydroxy-Δ^8.11.13-5β.10α-podocarpatrien-15-saeure 
• 5572-82-7 (+/-)-14-Oxo-5β,8α,9β,10α-podocarpan-19-saeuremethylester 
• 5095-23-8 (+/-)-14-Oxo-8β-formylmethyl-5β,9β,10α-podocarpan-19-saeuremethylester 

Downstream Products

• 5524-25-4 C₂₁H₃₂O₂ 
• 5524-25-4 kaurenoic acid methyl ester 
• 22338-69-8 15α-hydroxy-ent-kaur-16-en-19-oic acid 
• 6619-95-0 15-β-hydroxy-ent-kaur-16-en-19-oic acid 
• 58648-79-6 17α,19-Dihydroxy-ent-kauran 
• 3301-61-9 16α,17-dihydroxykauran-19-oic acid 
• 93888-88-1 ent-15β,16β-epoxy-17-hydroxykauran-19-oic acid 
• 250718-33-3 C₂₁H₃₄O₃ 
• 250718-32-2 methyl ent-15β-hydroxy-16α-kauran-19-oate 
• 78037-84-0 methyl ent-15-oxokauran-19-oate 
• 77970-49-1 methyl ent-15α-hydroxykauran-19-oate 
• 22376-47-2 methyl ent-15-oxokaur-16-en-19-oate 
• 10244-92-5 16β-hydro-ent-kauran-17,19-dioic acid 

Relevant academic research and scientific papers

BIOSYNTHESIS OF GIBBERELLIN A12-ALDEHYDE, GIBBERELLIN A12 AND THEIR KAURENOID PRECURSORS FROM MEVALONIC ACID IN A CELL-FREE SYSTEM FROM IMMATURE SEED OF PHASEOLUS COCCINEUS

A cell-free system capable of gibberellin (GA) biosynthesis has been prepared from immature seed of Phaseolus coccineus.This system converted mevalonic acid (MVA) to ent-kaurene, ent-kaurenoic acid, ent-kauradienoic acid, ent-7α-hydroxykaurenoic acid, ent-6α,7α-dihydroxykaurenoic acid, GA12-aldehyde and GA12. ent-Kaurene was converted to ent-kaurenol, ent-kaurenal, ent-kaurenoic acid and ent-7α-hydroxykaurenoic acid.All identifications were by GC/MC.The pathway from MVA to GA12-aldehyde in this species thus appears to be the same as that found in cell-free preparations derived from immature seed of other species.Key Word Index-Phaseolus coccineus; Leguminosae; runner bean; seed development; biosynthesis; cell-free system; HPLC; GC/MC; gibberellin.

KAURENOLIDE BIOSYNTHESIS IN A CELL-FREE SYSTEM FROM CUCURBITA MAXIMA SEEDS

A new product obtained by incubation of -mevalonic acid with a cell-free system from Cucurbita maxima endosperm was identified by GC-MS as ent-kaura-6,16-dien-19-oic acid.When this compound was reincubated with the microsomal fraction it was converted to 7β-hydroxykaurenolide and hence to 7β,12α-dihydroxykaurenolide.The dienoic acid was also obtained by incubation of ent-kaurene, ent-kaurenol, ent-kaurenal and ent-kaurenoic acid, but not ent-7α-hydroxykaurenoic acid, with the microsomal fraction.Thus, in the C. maxima cell-free system, the kaurenolides are formed by a pathway which branches from the GA pathway at ent-kaurenoic acid and proceeds via the dienoic acid.Key Word Index- Cucurbita maxima; Cucurbitaceae; biosynthesis; cell-free system; kaurenolides; gibberellins; ent-kaura-6,16-dien-19-oic acid.