Your Aunt can teach you Organic Opectroscopy

Organic spectroscopy should be brushed up and you get confidence

read my blog

 

Organic chemists from Industry and academics to interact on Spectroscopy techniques for Organic compounds ie NMR, MASS, IR, UV Etc. email me ……….. amcrasto@gmail.com

http://orgspectroscopyint.blogspot.in/  is the link

feder-0005.gif from 123gifs.euamcrasto@gmail.com

Oleanolic acid spectral data and interpretation

 http://orgspectroscopyint.blogspot.in/2014/08/oleanolic-acid-spectral-data-and.html
Chemical structure for Oleanolic AcidOleanolic acidOleanolic acid
(4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid

Oleanic acid, Caryophyllin, Astrantiagenin C, Giganteumgenin C, Virgaureagenin B, 3beta-Hydroxyolean-12-en-28-oic acid, OLEANOLIC_ACID
Molecular Formula: C30H48O3
Molecular Weight: 456.70032

http://orgspectroscopyint.blogspot.in/2014/08/oleanolic-acid-spectral-data-and.html

Ursolic acid [(3b)-3-Hydroxyurs-12-en-28-oic acid] rarely occurs without its isomer oleanolic acid [(3b)-3-Hydroxyolean-12-en-28-oic acid] They may occur in their free acid form, as shown in Figure 1, or as aglycones for triterpenoid saponins which are comprised of a triterpenoid aglycone linked to one or more sugar moieties. Ursolic and oleanolic acids are similar in pharmacological activity

A pentacyclic triterpene that occurs widely in many PLANTS as the free acid or the aglycone for many SAPONINS. It is biosynthesized from lupane. It can rearrange to the isomer, ursolic acid, or be oxidized to taraxasterol and amyrin.

MS
EIMS m/z (rel. int.) 456 [M]+ (5), 412 (3), 248 (100), 203 (50), 167 (25), 44 (51)

IR KBR
(KBr) 3500, 2950, 2850, 1715; 1H-NMR (250 MHz, pyridine-d5) δ: 5.49 (1H, s, H-12), 3.47 (1H, t, J = 8.0 Hz, H-3), 3.30 (1H, m, H-18), 1.12 (3H, s, CH3-27), 0.96 (3H, s, CH3-30), 0.91 (3H, s, CH3-25), 0.89 (3H, s, CH3-23), 0.87 (3H, s, CH3-24), 0.75 (3H, s, CH3-26)

http://orgspectroscopyint.blogspot.in/2014/08/oleanolic-acid-spectral-data-and.html

1H NMR

(250 MHz, pyridine-d5)δ: 5.49 (1H, s, H-12), 3.47 (1H, t, J = 8.0 Hz, H-3), 3.30 (1H, m, H-18), 1.12 (3H, s, CH3-27), 0.96 (3H, s, CH3-30), 0.91 (3H, s, CH3-25), 0.89 (3H, s, CH3-23), 0.87 (3H, s, CH3-24), 0.75 (3H, s, CH3-26)

13 C NMR

(63 MHz, pyridine-d5) δ: 180.2 (C-28), 144.8 (C-13), 122.5 (C-12), 78.0 (C-3), 55.7 (C-5), 48.0 (C-9), 46.6 (C-8, 17), 42.1 (C-14), 39.7 (C-4), 39.4 (C-1), 37.3 (C-10), 33.2 (C-7), 32.9 (C-29), 32.4 (C-21), 30.9 (C-20), 28.7 (C-23), 27.2 (C-2), 26.9 (C-15), 26.1 (C-30), 23.7 (C-11), 23.6 (C-16), 18.7 (C-6), 17.4 (C-26), 16.5 (C-24), 15.5 (C-25)

http://orgspectroscopyint.blogspot.in/2014/08/oleanolic-acid-spectral-data-and.html

http://www.google.com/patents/US20120237629

FIG. 4 shows the 1H NMR spectrum of oleanolic acid;
FIG. 5 shows the 13C NMR spectrum of oleanolic acid;
FIG. 6 shows the 13C DEPT NMR spectrum of oleanolic acid;
FIG. 7 shows the 113C HSQC NMR spectrum of oleanolic acid;
see below

http://orgspectroscopyint.blogspot.in/2014/08/oleanolic-acid-spectral-data-and.html

EXAMPLE 2 Extraction and Isolation of Oleanolic Acid (9) and Maslinic Acid (10) from Cloves

Syzygium aromaticum dried buds or whole cloves were obtained commercially. The cloves (1.5 kg, whole) of Syzygium aromaticum were sequentially and exhaustively extracted with hexane and ethyl acetate to give, after solvent removal in vacuo, a hexane extract (68.8 g, 4.9%) and an ethyl acetate extract (34.1 g, 2.3%). A portion of the ethyl acetate extract (10.0 g), was subjected to chromatographic separation on silica gel (60-120 mesh) column (40×5.0 cm). Elution with hexane/ethyl acetate solvent mixtures (8:2→6:4) afforded pure oleanolic acid (9) (4.7 g, 1.06%), a mixture of oleanolic acid (9) and maslinic acid (10) (0.5 g), and pure maslinic acid (10) (0.25 g). The structures of oleanolic acid (9) and maslinic acid (10) (as 2,3-diacetoxyoleanolic acid) were confirmed by spectroscopic data analysis (1D and 2D 1H NMR and 13C NMR experiments) (FIGS. 4-7 and FIGS. 8-10, respectively).
ANTHONY MELVIN CRASTO

THANKS AND REGARD’S
DR ANTHONY MELVIN CRASTO Ph.D

amcrasto@gmail.com

MOBILE-+91 9323115463
GLENMARK SCIENTIST ,  INDIA
web link
アンソニー     安东尼   Энтони    안토니     أنتوني
blogs are
 

 MY CHINA, VIETNAM  AND JAPAN BLOGS

http://me.zing.vn/u/amcrasto

ICELAND, RUSSIA, ARAB

BOBRDOBRBLAND ICELAND100zakladokadfty

GROUPS

you can post articles and will be administered by me on the google group which is very popular across the world

OPD GROUPSPACESSCOOP OCIorganic-process-development GOOGLE, TVINX, MENDELEY WDT,SCIPEOPLE OPD,EPERNICUS OPDSYNTHETIC ORGANIC CHEMISTRYLinkedIn group, DIIGO OPD,LINKEDIN OPD, WDT LINKEDIN, WDTI ZING

shark

 

 

Leave a Reply

Fill in your details below or click an icon to log in:

WordPress.com Logo

You are commenting using your WordPress.com account. Log Out / Change )

Twitter picture

You are commenting using your Twitter account. Log Out / Change )

Facebook photo

You are commenting using your Facebook account. Log Out / Change )

Google+ photo

You are commenting using your Google+ account. Log Out / Change )

Connecting to %s