AcO. O OAc OCH 3. Compound Number. (chloroform) Notes: M. Mozuch #36/46/Ac 21 mg. Acetone DMSO. CDCl 3. Atom

Transcript

1 Copoun Nuber 3 C DMS c c C 3 C c C= c C= ,3-Dacetoxypropoveratrone,3-acetoxy-3',4'-ethoxypropophenone (chlorofor) Shft , 7.9., , ,.0 Note: M. Mozuch #//c g FPL/DFRC NMR Databae -- Noveber 04

2 Copoun Nuber 3 C DMS...8 C 3 C C 3 C 3 C threo (3,4-Dethoxyphenyl)--[4-(-hyroxyethyl)-,-ethoxy phenoxy]propane-,3-ol (chlorofor) Shft q.4 8.7, Note: S. Ralph III- 0g FPL/DFRC NMR Databae -- Noveber 04

3 Copoun Nuber 3 3 C DMS c c C 3 C 3 C erythro Veratrylglycerol--guaacyl ether acetate c C= c C= ,3-acetoxy--(3,4-ethoxyphenyl)--(-ethoxyphenoxy) propane (chlorofor) Shft , 4.0.9, Note: L. Lanucc g threo ata n acetone FPL/DFRC NMR Databae -- Noveber 04

4 Copoun Nuber 4 3 C DMS p-yroxybenzyl alcohol 4-hyroxybenzyl alcohol (chlorofor) Shft 4. 3,.8, 7. Note:. Ralph: R 9. 0g Not very oluble n CDCL3 FPL/DFRC NMR Databae -- Noveber 04

5 Copoun Nuber 3 C DMS C C ,4-Dethoxybenzyl alcohol 3,4-ethoxybenzyl alcohol (chlorofor) Shft Note:. Ralph: R 9.4 0g FPL/DFRC NMR Databae -- Noveber 04

6 Copoun Nuber 3 C DMS C p-yroxyacetophenone 4-hyroxyacetophenone (chlorofor) Shft.0 3, , Note:.Ralph: R 9. 0g FPL/DFRC NMR Databae -- Noveber 04

7 Copoun Nuber 7 3 C DMS C C cetovanllone 4-hyroxy-3-ethoxyacetophenone (chlorofor) Shft Note:. Ralph: R 9. 0g FPL/DFRC NMR Databae -- Noveber 04

8 Copoun Nuber 8 3 C DMS C C 3 C cetoyrngone 3,-ethoxy-4-hyroxyacetophenone (chlorofor) Shft , 7. Note:. Ralph: R 9.3 g FPL/DFRC NMR Databae -- Noveber 04

9 Copoun Nuber 9 3 C DMS C C C cetoveratrone 3,4-ethoxyacetophenone (chlorofor) Shft ,.0 Note:. Ralph: R 9.4 g FPL/DFRC NMR Databae -- Noveber 04

10 Copoun Nuber 0 3 C DMS C (4-yroxyphenyl)ethanol -(4-hyroxyphenyl)ethanol (chlorofor) Shft q. 3,.8 8., Note:. Ralph: R 97. g lot noluble n CDCl3 FPL/DFRC NMR Databae -- Noveber 04

11 Copoun Nuber 3 C DMS C C pocynol -(4-hyroxy-3-ethoxyphenyl)ethanol (chlorofor) Shft Me q Note:. Ralph: R 97. FPL/DFRC NMR Databae -- Noveber 04

12 Copoun Nuber 3 C DMS C C 3 C (4-yroxy-3,-ethoxyphenyl)ethanol -(4-hyroxy-3,-ethoxyphenyl)ethanol (chlorofor) Shft q.4,.8 Note:. Ralph: R 97.3 FPL/DFRC NMR Databae -- Noveber 04

13 Copoun Nuber 3 3 C DMS C C C (3,4-Dethoxyphenyl)ethanol -(3,4-ethoxyphenyl)ethanol (chlorofor) Shft q Note:. Ralph: R 97.4 FPL/DFRC NMR Databae -- Noveber 04

14 Copoun Nuber 4 3 C DMS p-yroxybenzalehye 4-hyroxybenzalehye (chlorofor) Shft 3, , acetone 3, 7.00, Note:. Ralph: R 87. g FPL/DFRC NMR Databae -- Noveber 04

15 Copoun Nuber 3 C DMS C Vanlln 4-hyroxy-3-ethoxybenzalehye (chlorofor) Shft acetone b Note:. Ralph: R 87. g FPL/DFRC NMR Databae -- Noveber 04

16 Copoun Nuber 3 C DMS C 3 C Syrngyl alcohol 4-hyroxy-3,-ethoxybenzyl alcohol (chlorofor) Shft ,.0 Note:. Ralph: R 9.3 g lot noluble n acetone. FPL/DFRC NMR Databae -- Noveber 04

17 Copoun Nuber 7 3 C DMS C C c C= Methyl 4-acetoxybenzoate 4-acetoxybenzoc ac ethyl eter (chlorofor) Shft , , Note: L. Lanucc 3g FPL/DFRC NMR Databae -- Noveber 04

18 Copoun Nuber 8 3 C DMS C Methyl 4-hyroxybenzoate 4-hyroxybenzoc ac ethyl eter (chlorofor) Shft , , Note: lrch g FPL/DFRC NMR Databae -- Noveber 04

19 Copoun Nuber 9 3 C DMS C yroxy-3-ethoxybenzyl alcohol 4-hyroxy-3-ethoxybenzyl alcohol (chlorofor) Shft Note: lrch 4g FPL/DFRC NMR Databae -- Noveber 04

20 Copoun Nuber 3 C DMS C 3 p-nc ac 4-ethoxybenzoc ac (chlorofor) Shft ,.9 9.0, Note: lrch g FPL/DFRC NMR Databae -- Noveber 04

21 Copoun Nuber 3 C DMS C 3 C 3 C 3 C (,-Dethoxyphenoxy)-3-hyroxy--(4-hyroxy-3,- ethoxyphenyl)propan--one (chlorofor) Shft ,.7, 7., t 8.4 Note: a acetyl pperne n aple.. Ralph R7.P g - proton couple to ', hft not eterne. FPL/DFRC NMR Databae -- Noveber 04

22 Copoun Nuber 3 C DMS C 3 C C 3 C (,-Dethoxyphenoxy)--(4-hyroxy-3,-ethoxy phenyl)ethanone (chlorofor) Shft , 7., t 8.4 Note:. Ralph R7.P g FPL/DFRC NMR Databae -- Noveber 04

23 Copoun Nuber 3 C DMS c C c c C= c C= yroxyphenylethanol acetate -acetoxy--(4-acetoxyphenyl)ethane Shft q. 3, , Note:. Ralph R93. g FPL/DFRC NMR Databae -- Noveber 04

24 Copoun Nuber 3 C DMS c c 4 c C= c C= p-yroxybenzyl alcohol acetate 4-acetoxybenzyl acetate (chlorofor) Shft , , 7. Note: S. Ralph SRIII- g FPL/DFRC NMR Databae -- Noveber 04

25 Copoun Nuber 3 C DMS C C 3 Methyl-p-anate ethyl 4-ethoxybenzoate (chlorofor) Shft ,, Note: S. Ralph SRIII- 0g FPL/DFRC NMR Databae -- Noveber 04

26 Copoun Nuber 3 C DMS...0 C 3 C 3 C 3 c C (4-acetoxy-3,-ethoxyphenyl)--(,-ethoxyphenoxy) ethanone (chlorofor) c C= Shft Αχ Με. Β ΟΜε 3.80 Α ΟΜε Α, 7. Β, Β 7.0 t 8.4 Note:. Ralph GV. g FPL/DFRC NMR Databae -- Noveber 04

27 Copoun Nuber 3 C DMS C 3 c C 3 C c C= (4-acetoxy-3,-ethoxyphenyl)--(-ethoxyphenoxy) ethanone (chlorofor) Shft, Note:. Ralph GV. g FPL/DFRC NMR Databae -- Noveber 04

28 Copoun Nuber 3 C DMS C 3 C Dehyrovanlln,'-Dhyroxy-,'-ethoxybphenyl-3,3'-carbalehye (DMS) Shft = = Note:. Ralph KM 77. g contan purte th copoun ha a plane of yetry The hft for the other half are entcal. FPL/DFRC NMR Databae -- Noveber 04

29 Copoun Nuber 3 C DMS c c C 3 c C 3 C C 3 C Veratrylglycerol--yrngol ether tracetate,3-acetoxy--(3,4-ethoxyphenyl)--(4-(-acetoxyethyl)-,-ethoxyphenoxy)propane (chlorofor) threo c C=0 c C= c C= Shft q.7, , Note: S. Ralph III-4 g aple ha purte proton hen by ' FPL/DFRC NMR Databae -- Noveber 04

30 Copoun Nuber 3 C DMS n 0. Xylan Xylan,rch (DMS) Shft Note: IPC Xylan g - Quanttatve run - Run at 3K hft at 8.94 an 0.4 are for en group FPL/DFRC NMR Databae -- Noveber 04

31 Copoun Nuber 3 3 C DMS C C 3 C threo (3,4-Dethoxyphenyl)--[4-(-hyroxyethyl) phenoxy] propane-,3- ol (DMS) Shft Note: S. Ralph SR-7 g hft for nor erythro oer: C D.,.94, ,73.8, ,83.7,8.98 FPL/DFRC NMR Databae -- Noveber 04

32 Copoun Nuber 3 C DMS c c C 3 C 3 c C threo ,3-acetoxy--(3,4-ethoxyphenyl)--[4-(-acetoxyethyl) phenoxy] propane c C=0 c C= c C= (chlorofor) Shft ,..9, q.. Note: S. Ralph SR III-7C g hft for nor erythro oer: C D.9,3., ,74.4, ,78.93,7.9 FPL/DFRC NMR Databae -- Noveber 04

33 Copoun Nuber 3 C DMS c c C 3 C 3 C 3 c C threo ,3-acetoxy--(3,4-ethoxyphenyl)--[4-(-acetoxyethyl)--ethox yphenoxy] propane (chlorofor) c C= c C= c C= Shft , 4.0.9, q..7 Note: S. Ralph SR III-C g Shft for nor oer: C D.74,3., ,74.7, ,80.,78. FPL/DFRC NMR Databae -- Noveber 04

34 Copoun Nuber 3 C DMS C 3 C 3 C 3 C threo (3,4-ethoxyphenyl)--[4-(-hyroxyethyl)--ethoxy phenoxy] propane-,3-ol (chlorofor) Shft q Note: S. Ralph SR III- g hft for nor oer: C D 0.8,.8, ,73.,7. b 87.0,8.0,83.8 FPL/DFRC NMR Databae -- Noveber 04

35 Copoun Nuber 3 C DMS C Dhyroferulc c 3-(4-hyroxy-3-ethoxyphenyl)propanoc ac (chlorofor) Shft.4 t t Note:. bt g FPL/DFRC NMR Databae -- Noveber 04

36 Copoun Nuber 3 C DMS C C 3 4-Methoxyacetophenone 4-ethoxyacetophenone (chlorofor) Shft , , Note: lrch 7g FPL/DFRC NMR Databae -- Noveber 04

37 Copoun Nuber 3 C DMS C 3 p-methoxybenzyl alcohol 4-ethoxybenzyl alcohol (chlorofor) Shft ,.8 8.7, Note: lrch g FPL/DFRC NMR Databae -- Noveber 04

38 Copoun Nuber 3 C DMS Phenol phenol (chlorofor) Shft 3,.84.93, 7. Note: lrch R 8-4g FPL/DFRC NMR Databae -- Noveber 04

39 Copoun Nuber 3 C DMS C Guaacol -ethoxyphenol (chlorofor) Shft Note: lrch R 8. 4g FPL/DFRC NMR Databae -- Noveber 04

40 Copoun Nuber 3 C DMS C 3 C Syrngol,-ethoxyphenol (chlorofor) Shft , t 8. Note: lrch R 8.3 g FPL/DFRC NMR Databae -- Noveber 04

41 Copoun Nuber 4 3 C DMS C 3 C Syrngalehye 3,-ethoxy-4-hyroxybenzalehye (chlorofor) Shft 3.9, acetone 3.9, b Note:. Ralph R87.3 g Poor olublty FPL/DFRC NMR Databae -- Noveber 04

42 Copoun Nuber 3 C DMS C Vanllc ac 4-hyroxy-3-ethoxy benzoc ac (chlorofor) Shft ,.9 Note:. Ralph R89. g not very oluble n CDCl3 FPL/DFRC NMR Databae -- Noveber 04

43 Copoun Nuber 3 C DMS C 3 C Syrngc ac 3,-ethoxy-4-hyroxybenzoc ac (chlorofor) Shft 3.9, 7. Note:. Ralph R 89-3 g not very oluble n CDCl3 FPL/DFRC NMR Databae -- Noveber 04

44 Copoun Nuber 3 C DMS C C Veratrc ac 3,4-ethoxybenzoc ac (chlorofor) Shft ,.9 Note:. Ralph R 89-4 g FPL/DFRC NMR Databae -- Noveber 04

45 Copoun Nuber 3 C DMS p-couarc ac 4-hyroxycnnac ac tran (DMS) Shft ,.83 8., Note: Fluka 0g *not oluble n CDCl3 FPL/DFRC NMR Databae -- Noveber 04

46 Copoun Nuber 3 C DMS C 3 C Snapnc ac 3,-ethoxy-4-hyroxycnnac ac tran (DMS) Shft 3.83, Note: Lancater Synthe 0g *not very oluble n CDCl3 FPL/DFRC NMR Databae -- Noveber 04

47 Copoun Nuber 3 C DMS C 3 C ,4-Dethoxycnnac ac 3,4-ethoxycnnac ac tran (chlorofor) Shft , Note: K & K Lab 0g FPL/DFRC NMR Databae -- Noveber 04

48 Copoun Nuber 3 C DMS C Ferulc ac 4-hyroxy-3-ethoxycnnac ac tran (DMS) Shft , Note: lrch 0g not very oluble n CDCl3 Note:.0 wa run n 4-Me..,.7,.89,.,.94.77,.89,.,0.,70.93 FPL/DFRC NMR Databae -- Noveber 04

49 Copoun Nuber 3 C DMS C Methoxycnnac ac 4-ethoxycnnac ac tran (chlorofor) Shft 3.8 3, , Note: lrch g not CDCl3 oluble FPL/DFRC NMR Databae -- Noveber 04

50 Copoun Nuber 0 3 C DMS C 3 C 3 C Syrngylglycol--guaacyl ether (3,-ethoxy-4-hyroxyphenyl)--(-ethoxyphenoxy) ethanol (chlorofor) Shft , t , 3.0,. Note: S. Ralph SG g g FPL/DFRC NMR Databae -- Noveber 04

51 Copoun Nuber 3 C DMS C C 3 C 3 C (4-cetylphenoxy)--(3,4,-trethoxyphenyl)ethanone (chlorofor) Shft.4 3, , 7. 3,.9 8.9, Note: L. Lanucc LLL XVII 9 g contan trace purty FPL/DFRC NMR Databae -- Noveber 04

52 Copoun Nuber 3 C DMS C 3 C 3 C 3 C 3 C (4-cetyl--ethoxyphenoxy)--(3,4,-trethoxyphenyl) ethanone (chlorofor) Shft , , ,.9 Note: L. Lanucc LLL XVII 9c.g trace purty preent FPL/DFRC NMR Databae -- Noveber 04

53 Copoun Nuber 3 3 C DMS... C 3 C C 3 C 3 C 3 C (4-cetyl-,-ethoxyphenoxy)--(3,4,-trethoxyphenyl) ethanone (chlorofor) Shft 3, 3, 4,, Note: L. Lanucc LLL XVII 9 g FPL/DFRC NMR Databae -- Noveber 04

54 Copoun Nuber 4 3 C DMS C 3 nole Methoxybenzene (chlorofor) Shft ,,.90, 7. Note: lrch g FPL/DFRC NMR Databae -- Noveber 04

55 Copoun Nuber 3 C DMS C 3 C 3 C ,,3-trethoxybenzene (chlorofor) Shft 3, , t 8.3 Note: lrch g FPL/DFRC NMR Databae -- Noveber 04

56 Copoun Nuber 3 C DMS C 3 C 3 Veratrole,-ethoxybenzene (chlorofor) Shft 3.8,.89,.89 Note: lrch g FPL/DFRC NMR Databae -- Noveber 04

57 Copoun Nuber 7 3 C DMS C 3 C Veratralehye 3,4-ethoxybenzalehye (chlorofor) Shft , Note: lrch g FPL/DFRC NMR Databae -- Noveber 04

58 Copoun Nuber 8 3 C DMS hyroxybenzoc ac (DMS) Shft 3,.8 8.8, Note: lrch g *CDCl3 noluble FPL/DFRC NMR Databae -- Noveber 04

59 Copoun Nuber 9 3 C DMS C C ethyl (4-ethoxy)cnnaate (chlorofor) Shft , , Note:. Ralph PS x 9g FPL/DFRC NMR Databae -- Noveber 04

60 Copoun Nuber 0 3 C DMS C C 3 C Methyl Snapate ethyl (3,-ethoxy-4-hyroxy)cnnaate tran (chlorofor) Shft , 3.90, Note:. Ralph RPS x g FPL/DFRC NMR Databae -- Noveber 04

61 Copoun Nuber 3 C DMS C Methyl p-couarate ethyl 4-hyroxycnnaate tran (chlorofor) Shft ,.8 8.7, Note:. Ralph RPS.x 8g FPL/DFRC NMR Databae -- Noveber 04

62 Copoun Nuber 3 C DMS C C 3 C 3 C tran ethyl (3,4,-trethoxy)cnnaate (chlorofor) Shft 3, 4, Note:. Ralph RPS x 9g FPL/DFRC NMR Databae -- Noveber 04

63 Copoun Nuber 3 3 C DMS b C 3 C 3 C tran 3,4,-trethoxy cnnac ac (chlorofor) Shft 3, , Note: lrch g FPL/DFRC NMR Databae -- Noveber 04

64 Copoun Nuber 4 3 C DMS C C 3 C Syrngc ac ethyl eter ethyl (4-hyroxy-3,-ethoxy)benzoate (chlorofor) Shft 3,, Note:. Ralph RPS 7x 93.3g FPL/DFRC NMR Databae -- Noveber 04

65 Copoun Nuber 3 C DMS C C Vanllc ac ethyl eter ethyl (3-ethoxy-4-hyroxy)benzoate (chlorofor) Shft ,.8 Note:. Ralph RPS 3. 0g FPL/DFRC NMR Databae -- Noveber 04

66 Copoun Nuber 3 C DMS C C C C Dhyroehyrooeugenol -Methoxy-4-(7-ethoxy-3-ethyl--propyl-,3-hyro benzofuran-- yl)phenol (chlorofor) Shft 0.9. t t , Note:. Ralph RL 09x g FPL/DFRC NMR Databae -- Noveber 04

67 Copoun Nuber 7 3 C DMS C C C C Dehyrooeugenol Methoxy-4-(7-ethoxy-3-ethyl--propenyl-,3-hyro benzofuran--yl) phenol (chlorofor) Shft ,. 3. t 9.4, q.8,.3. q.8, Note:. Ralph RKM 7-0g FPL/DFRC NMR Databae -- Noveber 04

68 Copoun Nuber 8 3 C DMS C C Methyl ferulate ethyl 4-hyroxy-3-ethoxycnnaate tran (chlorofor) Shft ,.8..9 Note:. Ralph RKM 8. 4g FPL/DFRC NMR Databae -- Noveber 04

69 Copoun Nuber 9 3 C DMS C C C Methylveratrate ethyl 3,4-ethoxybenzoate (chlorofor) Shft ,.9 Note:. Ralph RPS. g FPL/DFRC NMR Databae -- Noveber 04

70 Copoun Nuber 70 3 C DMS C C 3 C tran ethyl 3,4-ethoxycnnaate (chlorofor) Shft , Note:. Ralph RPS x g FPL/DFRC NMR Databae -- Noveber 04

71 Copoun Nuber 7 3 C DMS C 3 C C 3 C Dehyroveratralehye,,','-Tetraethoxybphenyl-3,3'-carbalehye (chlorofor) Shft acetone Note: bt g contan purty th copoun ha a plane of yetry The hft for the other half are entcal. FPL/DFRC NMR Databae -- Noveber 04

72 Copoun Nuber 7 3 C DMS C 3 C 3 C 3 C Dehyroveratrc ac,,','-tetraethoxybphenyl-3,3'-carboxylc ac (DMS) Shft Note: bt g * only oluble n DMS * alehye purty th copoun ha a plane of yetry The hft for the other half are entcal. FPL/DFRC NMR Databae -- Noveber 04

73 Copoun Nuber 73 3 C DMS C C C C 3 C (3,4-Dethoxyphenyl)-7-ethoxy-3-ethyl--propyl-,3- hyrobenzofuran (chlorofor) Shft 0.9. t h t q , ,.9.9 Note: bt g FPL/DFRC NMR Databae -- Noveber 04

74 Copoun Nuber 74 3 C DMS c c c C 3 C Guaacylglycerol--guaacyl ether tracetate threo -(4-acetoxy-3-ethoxyphenyl)-,3-acetoxy--(-ethoxy phenoxy)propane c C= c C= c C= (chlorofor) Shft ,.7.9, 4..3 Note: R. el RFC 0g FPL/DFRC NMR Databae -- Noveber 04

75 Copoun Nuber 7 3 C DMS c C 3 C c C 3 C C c C 3 C C (4-cetoxy-3-ethoxyphenyl) acrylc ac 3-acetoxy- 3- (4- acetoxy-3 -ethoxyphenyl)--(-ethoxyphenoxy) propyl eter (chlorofor) Shft threo C 4 C4 C C3 C c C= c C= c C= ,..9, 4.. C C Note: R. el RF0D g Vnyl C' at.08 an. n acetone. In CDCl3. an. ata n. g. Foo Che. 4(4) 70-7, 993 FPL/DFRC NMR Databae -- Noveber 04

76 Copoun Nuber 7 3 C DMS c C 3 C c C 3 C C c C 3 C C (4-cetoxy-3-ethoxyphenyl) acrylc ac 3-acetoxy- 3-(4- acetoxy-3- ethoxyphenyl)--(-ethoxyphenoxy) propyl eter (chlorofor) Shft erythro C 4 C4 C C3 C c C= c C= c C= , 4..9,.3. C C Note: R. el RF0D g Vnyl C' at.09 an.3 n acetone ata n. g. Foo Che. 4(4) 70-7, 993 FPL/DFRC NMR Databae -- Noveber 04

77 Copoun Nuber 77 3 C DMS c C c c C 3 C 3 C C3 C erythro C C (4-cetoxyphenyl) acrylc ac 3-acetoxy--(4-acetoxy- 3-ethoxyphe nyl)--(-ethoxyphenoxy)propyl eter C (chlorofor) Shft.0.. C C4 C , 4.3.9,.9.0 c C= c C= c C= C..0 C, C3, C 7..0 Note: R. el RF9D g FPL/DFRC NMR Databae -- Noveber 04

78 Copoun Nuber 78 3 C DMS c C c c C 3 C 3 C C3 C threo C C (4-cetoxyphenyl) acrylc ac 3-acetoxy--(4-acetoxy- 3-ethoxyphe nyl)--(-ethoxyphenoxy)propyl eter C (chlorofor) Shft.0.. C C4 C ,.8.9, c C= c C= c C= C..0 C. C C 7..0 Note: R. el RF9D g FPL/DFRC NMR Databae -- Noveber 04

79 Copoun Nuber 79 3 C DMS C 3 C C 3 c C 3 C (4-acetoxy-3,-ethoxyphenyl)--(4-acetyl-,-ethoxy phenoxy) -3-hyroxypropan--one c C= (chlorofor) Shft..8 3, 3, , 3.3,, Note: SR III - g FPL/DFRC NMR Databae -- Noveber 04

80 Copoun Nuber 80 3 C DMS C C 3 c C (4-acetoxy-3,-ethoxyphenyl)--(4-acetylphenoxy)- 3-hyroxypropan--one c C= (chlorofor) Shft.. 3, , 4., 7. 3, , Note: SR III - g, an hft change place n DMS FPL/DFRC NMR Databae -- Noveber 04

81 Copoun Nuber 8 3 C DMS C 3 c C 3 C 3 C (4-acetoxy-3,-ethoxyphenyl)--(4-acetoxy--ethoxy phenoxy)-3-hyroxypropan--one (chlorofor) c C= Shft , t.., ,.0 Note: SR III - 7g an 4 wtch place n DMS 4 ha very low ntenty an eay to follow FPL/DFRC NMR Databae -- Noveber 04

82 Copoun Nuber 8 3 C DMS c C c c C 3 C 3 C C3 C threo C C cetoxycnnac ac 3-acetoxy-3-(4-acetoxy- 3-ethoxyphenyl)--( -ethoxyphenoxy)propyl eter C (chlorofor) Shft.07.. C C4 C ,.8.9, 4. c C= c C= c C= C C, C3, C 7..0 Note: R. el RF87D.g.8 an.7 for an C, change place n DMS ee 09 FPL/DFRC NMR Databae -- Noveber 04

83 Copoun Nuber 83 3 C DMS c C c c C 3 C 3 C C3 C erythro 4-cetoxycnnac ac 3-acetoxy-3-(4-acetoxy- 3-ethoxyphenyl)--( -ethoxyphenoxy)propyl eter C C C 4 C (chlorofor) Shft C C c C= c C= c C= , 4..9, C..0 C 7..0 Note: Rch el RF87D.g ee 0 FPL/DFRC NMR Databae -- Noveber 04

84 Copoun Nuber 84 3 C DMS c C 3 C c c C 3 C 3 C C erythro 3-(4-cetoxy-3-ethoxyphenyl)acrylc ac 4-[,3-acetoxy--(-eth oxyphenoxy)propyl]phenyl eter C C C 4 C4 C (chlorofor) Shft C C c C= c C= c C= , 4.0.9, C.0.9 C Note: R. el RF9D.4g ee 0 FPL/DFRC NMR Databae -- Noveber 04

85 Copoun Nuber 8 3 C DMS C C 3 C c c C 3 C 3 3-{4-[3-cetoxy--(4-acetoxy-3-ethoxyphenyl)--(-ethoxy phenoxy)propoxy]phenyl}acrylc ac ethyl eter C C3 C C C C 4 C (chlorofor) Shft C C= 4 C= C C..0 C3, C, C Note: R. el RFD.0 g Ioer of 8 FPL/DFRC NMR Databae -- Noveber 04

86 Copoun Nuber 8 3 C DMS C C 3 C c c C 3 C 3 3-{4-[3-cetoxy--(4-acetoxy-3-ethoxyphenyl)--(-ethoxy phenoxy)propoxy]phenyl}acrylc ac ethyl eter C C3 C C C C 4 C (chlorofor) Shft C C= 4 C= C 3.7 C ,.9.7, 4.3 C C, C Note: Rch el RFD g Ioer of 8 FPL/DFRC NMR Databae -- Noveber 04

87 Copoun Nuber 87 3 C DMS C Conferyl alcohol 4-hyroxy-3-ethoxy cnnayl alcohol tran Shft t. ' 4.8 t.,.. t.9,.. t.9, , Note: lrch g Proton ata fro 0 Mz pectru n acetone..s.q. FPL/DFRC NMR Databae -- Noveber 04

88 Copoun Nuber 88 3 C DMS C C 3 C 3 C threo (4-yroxy-3,-ethoxyphenyl)--[4-(-hyroxyethyl)-- ethoxyphenoxy]propane-,3-ol Shft , ,.77 Note: S Ralph SRIII- g Sall aount of 4 c preent. FPL/DFRC NMR Databae -- Noveber 04

89 Copoun Nuber 89 3 C DMS...84 C 3 C C 3 C 3 C threo (4-yroxy-3,-ethoxyphenyl)--[4-(-hyroxyethyl)-,-etho xyphenoxy]propane-,3-ol Shft..4 3, 3, ,.9,, Note: S Ralph SRIII- g FPL/DFRC NMR Databae -- Noveber 04

90 Copoun Nuber 90 3 C DMS C 3 C 3 C Syrngylglycerol--guaacyl ether threo -(4-yroxy-3,-ethoxyphenyl)--(-ethoxyphenoxy) propane-,3-ol Shft 3.8 3, , ,.8 Note: S. Ralph SRIII- g FPL/DFRC NMR Databae -- Noveber 04

91 Copoun Nuber 9 3 C DMS C C 3 C (4-yroxy-3,-ethoxyphenyl)--[4-(-hyroxy ethyl)phenoxy]propane-,3-ol Shft..4 3, 3.79,.77, Note: S. Ralph SRIII- g contan 4-C purty. FPL/DFRC NMR Databae -- Noveber 04

92 Copoun Nuber 9 3 C DMS C 3 c C 3 C c C= (4-acetoxy-3,-ethoxyphenyl)-3-hyroxy--(-ethoxy phenoxy)propan--one (chlorofor) Shft. 3, t.., 7. Note: S. Ralph SRIII- g * + 4 wtch aroun n CDCl3 FPL/DFRC NMR Databae -- Noveber 04

93 Copoun Nuber 93 3 C DMS Phenyl benzoate enzoc ac phenyl eter (chlorofor) Shft, Note: lrch 0g l change poton n DMS FPL/DFRC NMR Databae -- Noveber 04

94 Copoun Nuber 94 3 C DMS C C C Ethyl 4-hyroxybenzoate ethyl 4-hyroxybenzoate (chlorofor) Shft C3. t 7. C 4. q 7. 3,.9 8.8, Note: lrch 0g FPL/DFRC NMR Databae -- Noveber 04

95 Copoun Nuber 9 3 C DMS tran Cnnayl alcohol (E)-3-phenyl--propen--ol(E)-cnnayl alcohol (chlorofor) Shft 4..,.. t.9,..4 t.9,. Note: Fluka 0g FPL/DFRC NMR Databae -- Noveber 04

96 Copoun Nuber 9 3 C DMS Cnnaalehye (E)-3-phenyl--propenal(E)-cnnaalehye tran (chlorofor) Shft.9.0, Note: Fluka 0g FPL/DFRC NMR Databae -- Noveber 04

97 Copoun Nuber 97 3 C DMS c c C 3 c c C 3 C 3 C threo (4-acetoxy-3,-ethoxyphenyl)-,3-acetoxy--[4- (-acetoxyethyl)--ethoxyphenoxy] (chlorofor) Shft 4 c C= c C= c C= c C= , ,.7.8, q..,.7 Note: S. Ralph SRIII- g ca 90% threo * FPL/DFRC NMR Databae -- Noveber 04

98 Copoun Nuber 98 3 C DMS c c C 3 c C C 3 c C 3 C threo -(4-acetoxy-3,-ethoxyphenyl)-,3-acetoxy--[4- (-acetoxyethyl)-,-ethoxyphenoxy]propane (chlorofor) Shft 4 c C= c C= c C= c C= q.8, 7.3.8, 4...,,..70 Note: S. Ralph SRIII- 3g * FPL/DFRC NMR Databae -- Noveber 04

99 Copoun Nuber 99 3 C DMS c c C 3 c C 3 C 3 b threo -(4-acetoxy-3,-ethoxyphenyl)-,3-acetoxy--(-ethoxy phenoxy)propane 3 4 c C= c C= c C= Shft , ,..9, 4.., , 8.,.3 8.,.0 8.0,.3 8.0, 8.,.0 Note: S. Ralph SRIII- g ca 80% threo *Checal hft agnent for overlappng pattern, an,, an were ae wth the atance of econvoluton pectra obtane w th MacNut, corn NMR Inc. ll pattern were coplex ultplet (non- t orer) an eterne fro ulaton fle FPL/DFRC NMR Databae -- Noveber 04

100 Copoun Nuber 3 C DMS c c C 3 c C 3 c C threo -(4-acetoxy-3,-ethoxyphenyl)-,3-acetoxy--[4- (-acetoxyethyl)phenoxy] propane (chlorofor) Shft 4 c C= c C= c C= c C= , q.8,..8,-..3, 3,, Note: S. Ralph SRIII- g CDCl3 pectru poor * FPL/DFRC NMR Databae -- Noveber 04

101 Copoun Nuber 0 3 C DMS C C Guaacylglycerol--guaacyl ether erythro -(4-hyroxy-3-ethoxyphenyl)--(-ethoxyphenoxy)propan-,3-ol (chlorofor) Shft Note:. Ralph R 78.3 g. Ralph olzforchung (988) p3- FPL/DFRC NMR Databae -- Noveber 04

102 Copoun Nuber 0 3 C DMS C C Guaacylglycerol--guaacyl ether threo -(4-hyroxy-3-ethoxyphenyl)--(-ethoxyphenoxy)propane-,3-o l (chlorofor) Shft Note:. Ralph RGV.X g. Ralph olzforchung (988) p.3- FPL/DFRC NMR Databae -- Noveber 04

103 Copoun Nuber 03 3 C DMS C c C c C= cetylate acetovanllone 4-acetoxy-3-ethoxyacetophenone (chlorofor) Shft ,.9 Note: IPC g FPL/DFRC NMR Databae -- Noveber 04

104 Copoun Nuber 04 3 C DMS C 3 C 3 C threo Veratrylglycerol--guaacyl ether -(3,4-Dethoxyphenyl)--(-ethoxyphenoxy)propane-,3-ol (chlorofor) Shft Note: LL Lanucc 7g Shft reporte are for threo oernor oer of th xture. ee 0 alo FPL/DFRC NMR Databae -- Noveber 04

105 0 Copoun Nuber C 3 C 3 C 3 LL Lanucc g alpha proton 4. n acetone Note: FPL/DFRC NMR Databae -- Noveber 04 Veratrylglycerol--guaacyl ether -(3,4-Dethoxyphenyl)--(-ethoxyphenoxy)-propane-,3-ol 3 C DMS Shft acetone (chlorofor) erythro

106 0 Copoun Nuber C 3 C 3 S. Ralph g Note: FPL/DFRC NMR Databae -- Noveber 04 Erone 3-yroxy--(4-hyroxy-3-ethoxyphenyl)--(-ethoxy phenoxy)-propan--one 3 C DMS Shft t.. (chlorofor)

107 Copoun Nuber 07 3 C DMS C C Vanllyl--D-Glucoe -(4-yroxy-3-ethoxybenzyloxy)--hyroxyethyl tetrahyropyran-3,4,-trol Not run Shft Note: M.Mozuch 88/7/ g not oluble n CDCl3 FPL/DFRC NMR Databae -- Noveber 04

108 Copoun Nuber 08 3 C DMS c C c C= cetylate ferulc ac 4-acetoxy-3-ethoxycnnac ac (chlorofor) Shft Note: R. el RF 83F 0g not uluble n CDCL3 FPL/DFRC NMR Databae -- Noveber 04

109 Copoun Nuber 09 3 C DMS C 3 c c C c C= Pnorenol acetate cetc ac 4-[4-(4-acetoxy-3-ethoxyphenyl) tetrahyrofuro[3,4-c]fur an--yl]--ethoxyphenyl eter (chlorofor) Shft , , , Note:. Pew th copoun ha a plane of yetry The hft for the other half are entcal. FPL/DFRC NMR Databae -- Noveber 04

110 0 Copoun Nuber C 3 C 3 C 3 LL Lanucc g Note: FPL/DFRC NMR Databae -- Noveber 04 Veratrone -(3,4-Dethoxyphenyl)-3-hyroxy--(-ethoxyphenoxy) propan--one 3 C DMS Shft t ,.0 (chlorofor)

111 Copoun Nuber 3 C DMS C C c c C= acetylate oeugenol -(3-ethoxy-4-acetoxyphenyl)--propene (chlorofor) Shft.8., q.7,...7,.4 Note:. Ralph RPS. 0g FPL/DFRC NMR Databae -- Noveber 04

112 Copoun Nuber 3 C DMS C C Ioeugenol -(3-ethoxy-4-hyroxyphenyl)--propene (chlorofor) Shft.83.., q.7,...7,. Note: lrch 0g contan an purty FPL/DFRC NMR Databae -- Noveber 04

113 3 Copoun Nuber C 3 lrch 0g Note: FPL/DFRC NMR Databae -- Noveber 04 Eugenol 4-llyl--ethoxyphenol 3 C DMS 4 3 Shft t.. 8. (chlorofor)

114 Copoun Nuber 4 3 C DMS C 3 C llyl-,-ethoxyphenol (chlorofor) Shft , t.8, 0.,.7 Note: lrch 0g Extraneou peak aroun 0 an 9 FPL/DFRC NMR Databae -- Noveber 04

115 Copoun Nuber 3 C DMS C c c C= acetylate eugenol -(3-ethoxy-4-acetoxyphenyl)--propene (chlorofor) Shft t.8, 0., Note:. Ralph RC9. 0g FPL/DFRC NMR Databae -- Noveber 04

116 Copoun Nuber 3 C DMS C 3 c C c C= (3,-ethoxy-4-acetoxyphenyl)--propene (chlorofor) Shft , t.8, 0.,.7 Note:. Ralph RPS. 0g FPL/DFRC NMR Databae -- Noveber 04

117 Copoun Nuber 7 3 C DMS C C C C 3 Syrngylrenol (chlorofor) Shft ,.8 Note: IPC - Pearl 4g th copoun ha a plane of yetry The hft for the other half are entcal. FPL/DFRC NMR Databae -- Noveber 04

118 Copoun Nuber 8 3 C DMS C C Confern 4-(3-hyroxy--propenyl)--ethoxyphenyl-D-glucopyranoe (DMS) Shft 3.78, t.03.9, ,.8 7.3,3,4, nr t t. Note: IPC - Pearl 3g only oluble n DMS Teraha, Ralph, Lanucc olzforchung 0(99)p. - FPL/DFRC NMR Databae -- Noveber 04

119 Copoun Nuber 9 3 C DMS C 3 C C Syrngn 4-(3-hyroxy--propenyl)-,-ethoxy- -D-glucopyranoe (DMS) Shft t.0.9,4.7.9, ,3,4, nr t t. Note: IPC - Pearl 0g only oluble n DMS Teraha, Ralph, Lanucc olzforchung 0(99)p. - FPL/DFRC NMR Databae -- Noveber 04

120 Copoun Nuber 3 C DMS c c C c c c C Confern acetate 4-(3-hyroxy--propenyl)--ethoxy pheny-l -D-glycopyranoe pentaacetate (chlorofor) Shft 4 3 c C= c C= c C= c C= c C= t.8, b b Note: S. Ralph III-8 0g FPL/DFRC NMR Databae -- Noveber 04

121 Copoun Nuber 3 C DMS c C 3 C c c c c C Syrngn acetate 4-(3-hyroxy--propenyl)-,-ethoxy phenyl--d-glucopyrano e penta acetate (chlorofor) Shft c C= c C= c C= c C= c C= t.4.8,.4.8,. Note: S. Ralph III - 8 0g FPL/DFRC NMR Databae -- Noveber 04

122 Copoun Nuber 3 C DMS c c c c Xyloe cetate c C= c C= c C= c C= c C= c C= c C= c C= (chlorofor) Shft Note: S. Ralph III - 8 0g xture of + FPL/DFRC NMR Databae -- Noveber 04

123 Copoun Nuber 3 C DMS...07 C 3 c C C c C c C= Syrngylrenol acetate cetc ac 4-[4-(4-acetoxy-3,-ethoxyphenyl) tetrahyrofuro[3,4-c] furan--yl]-,-ethoxyphenyl eter (chlorofor) Shft , , ,.9 Note: S. Ralph III - 8 g th copoun ha a plane of yetry The hft for the other half are entcal. FPL/DFRC NMR Databae -- Noveber 04

124 Copoun Nuber 3 C DMS C c - Ferulc c (Z)-4-hyroxy-3-ethoxycnnac ac c (ethanol) Shft ,.0.0 Note:. bt g 7 a 3C n 4-Me. Dept wa run & arke on 7 not ave. FPL/DFRC NMR Databae -- Noveber 04

125 Copoun Nuber R C. g Note: FPL/DFRC NMR Databae -- Noveber 04 -(4-hyroxyphenyl)--phenoxyethanol 3 C DMS Shft , 3. (chlorofor)

126 Copoun Nuber 3 C DMS C 3 C (4-hyroxy-3-ethoxyphenyl)--(-ethoxyphenoxy)ethanol (chlorofor) Shft , , , 3.0 Note: R. g * 7.0 hft n CDCL3 fall uner olvent peak. FPL/DFRC NMR Databae -- Noveber 04

127 Copoun Nuber 3 C DMS Dhyrocouarc ac 3-(4-hyroxyphenyl)proponc ac (chlorofor) Shft.3 t t 7.0 3,.77 8., Note: IPC Pearl Coll. 0g FPL/DFRC NMR Databae -- Noveber 04

128 Copoun Nuber 3 C DMS c c C= acetylate hyrocouarc ac 3-(4-acetoxyphenyl)proponc ac (chlorofor) Shft..7 t t 7.3, , Note: IPC Pearl Coll. 0g Contan unacetylate cp alo FPL/DFRC NMR Databae -- Noveber 04

129 Copoun Nuber 3 C DMS c c C= acetylate couarc ac (E)-4-acetoxycnnac ac tran (chlorofor) Shft , 7. 8., Note: IPC Pearl coll. 0g FPL/DFRC NMR Databae -- Noveber 04

130 Copoun Nuber 3 C DMS C 3 c C 3 C c C= acetoxy--(4-hyroxy-3,-ethoxyphenyl)propan--one (chlorofor) Shft q 7.0, 7. Note: IPC Pearl coll. 0g FPL/DFRC NMR Databae -- Noveber 04

131 Copoun Nuber 3 3 C DMS C 3 C 3 C threo -(4-hyroxy-3-ethoxyphenyl)--[4-(-hyroxyethyl)-- ethoxyphenoxy]propane-,3-ol (chlorofor) Shft q Note: S. Ralph SRIII-- g erythro ata C D FPL/DFRC NMR Databae -- Noveber 04