2,3,23-Trihydroxy-12-oleanen-28-oic acid

Base Information

• Chemical Name: 2,3,23-Trihydroxy-12-oleanen-28-oic acid
• CAS No.: 102519-34-6
• Molecular Formula: C₃₀H₄₈O₅
• Molecular Weight: 488.708
• Mol file: 102519-34-6.mol

Synonyms:2a,3a,23-Trihydroxyolean-12-en-28-oic acid; Isoarjunolicacid

Chemical Property of 2,3,23-Trihydroxy-12-oleanen-28-oic acid

Chemical Property:

• Boiling Point: 606.0±55.0 °C(Predicted)
• PKA: 4.62±0.70(Predicted)
• PSA: 97.99000
• Density: 1.19±0.1 g/cm3(Predicted)
• LogP: 5.17680

Purity/Quality:

99% ^*data from raw suppliers

Isoarjunolicacid 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2,3,23-Trihydroxy-12-oleanen-28-oic acid

There total 55 articles about 2,3,23-Trihydroxy-12-oleanen-28-oic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 71.7%

bayogenin {28-O-α-L-rhamnopyranosyl-(1->2)-[β-D-galactopyranosyl(1->3)]-[β-D-glucopyranosyl-(1->6)]-β-D-glucopyranosyl} ester → D-quionovose (7658-08-4,478518-52-4) + D-glucose (50-99-7) + D-Galactose (59-23-4) + bayogenin (465-00-9,6989-24-8,87392-68-5,102519-34-6,106293-97-4,118711-55-0,150821-16-2)

Guidance literature:

bayogenin {28-O-α-L-rhamnopyranosyl-(1->2)-[β-D-galactopyranosyl(1->3)]-[β-D-glucopyranosyl-(1->6)]-β-D-glucopyranosyl} ester; With sulfuric acid; In 1,4-dioxane; for 1h; Reflux;

In 1,4-dioxane;

DOI:10.1248/cpb.59.889

Reference yield: 61.4%

desacylperennisoside XI → D-quionovose (7658-08-4,478518-52-4) + D-glucose (50-99-7) + D-Galactose (59-23-4) + bayogenin (465-00-9,6989-24-8,87392-68-5,102519-34-6,106293-97-4,118711-55-0,150821-16-2)

Guidance literature:

desacylperennisoside XI; With sulfuric acid; In 1,4-dioxane; for 1h; Reflux;

In 1,4-dioxane;

DOI:10.1248/cpb.59.889

Reference yield: 52.2%

desacyl-perennisoside VIII → D-quionovose (7658-08-4,478518-52-4) + D-Fucose (3615-37-0,478518-52-4) + D-glucose (50-99-7) + bayogenin (465-00-9,6989-24-8,87392-68-5,102519-34-6,106293-97-4,118711-55-0,150821-16-2)

Guidance literature:

desacyl-perennisoside VIII; With sulfuric acid; In 1,4-dioxane; for 1h; Reflux;

In 1,4-dioxane;

DOI:10.1248/cpb.59.889

upstream raw materials:

3-O-<α-L-arabinopyranosyl(1->2)-β-D-glucopyranosyl>-bayogenin

lobatoside C

undeca-acetate of medicoside J

3-O-β-D-glucopyranosyl-2β,3β,23-trihydroxyolean-12-en-28-oic acid-28-O-β-D-xylopyranosyl-(1→6)-[β-D-glucopyranosyl-(1→2)]-[β-D-glucopyranosyl-(1→3)]-β-D-glucopyranoside

Downstream raw materials:

C₃₀H₄₆O₅

C₃₂H₄₈O₆

olean-12-ene-2β,3β,23,28-tetraol

Barringtogenol

Refernces

• 1、 Barbosa, Antony De Paula,Da Silva, Bernadete Pereira,Parente, José Paz. "A new complex triterpenoid saponin from Samanea saman with haemolytic activity and adjuvant effect". . p. 626 - 631. Retrieved 2012.
• 2、 Morikawa, Toshio,Li, Xuezheng,Nishida, Eriko,Nakamura, Seikou,Ninomiya, Kiyofumi,Matsuda, Hisashi,Hamao, Makoto,Muraoka, Osamu,Hayakawa, Takao,Yoshikawa, Masayuki. "Medicinal flowers. XXXII.1) Structures of oleanane-type triterpene saponins, perennisosides VIII, IX, X, XI, and XII, from the flowers of Bellis perennis". . p. 889 - 895. Retrieved 2011.
• 3、 Mimaki, Yoshihiro,Watanabe, Kazuki,Matsuo, Yukiko,Sakagami, Hiroshi. "Triterpene glycosides from the tubers of Anemone coronaria". . p. 724 - 729. Retrieved 2009.
• 4、 Dorsaz, Anne-Christine,Hostettmann, Kurt. "Further SAponins from Phytolacca dodecandra L'HERIT". . p. 2038 - 2047. Retrieved 1986.
• 5、 Zhang,Miyase,Kuroyanagi,Umehara,Ueno. "Studies on the constituents of Polygala japonica HOUTT. I. Structures of polygalasaponins I-X". . p. 115 - 120. Retrieved 1995.
• 6、 Kasai, Ryoji,Miyakoshi, Masazumi,Nie, Rui-Lin,Zhou, Jun,Matsumoto, Kazuhiro,Morita, Toshinobu,Nishi, Masatoshi,Miyahara, Kazumoto,Tanaka, Osamu. "Saponins from Bolbostemma paniculatum: Cyclic bisdesmosides, tubeimosides II and III". . p. 1439 - 1446. Retrieved 1988.
• 7、 Su, Yanfang,Guo, Dean,Guo, Hongzhu,Liu, Jiansheng,Zheng, Junhua,Koike, Kazuo,Nikaido, Tamotsu. "Four new triterpenoid saponins from Conyza blinii". . p. 32 - 36. Retrieved 2001.
• 8、 Zhang,Miyase,Kuroyanagi,Umehara,Ueno. "Studies on the constituents of Polygala japonica HOUTT. II. Structures of polygalasaponins XI-XIX". . p. 966 - 970. Retrieved 1995.