Entry Name: Estra-1,3,5(10)-triene-3,17-diol
CRC Number: BBB24-E
Molecular Formula: C18H24O2
Molecular Weight: 272.386
Accurate Mass: 272.17763
Percentage Composition: C 79.37%; H 8.88%; O 11.75%
General Statement: Estradiol is the accepted U.S. and IUPAC spelling
InChi Key: VOXZDWNPVJITMN-UHFFFAOYSA-N
InChi: InChI=1S/C18H24O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6
-7-17(18)20/h3,5,10,14-17,19-20H,2,4,6-9H2,1H3

Variant: 17α-form
Synonym(s): Alfatradiol, INN. Estradiol-17α. β-Estradiol (obsol., misleading). Epiestradiol.
CRC Number: GQB96-F
CAS Registry Number: 57-91-0
Type of Compound Code(s): AJ2350  XA6240  AJ0100  VT0100 
Molecular Formula: C18H24O2
Molecular Weight: 272.386
Accurate Mass: 272.17763
Percentage Composition: C 79.37%; H 8.88%; O 11.75%
Biological Source: Isol. from pregnancy urine
Biological Use / Importance: Topical inhibitor of 5α-reductase
Physical Description: Needles (EtOH aq.)
Melting Point: Mp 223°     
Optical Rotation: [α] 18D  +56.7  ( EtOH)
Other Data: Less potent estrogen than the 17β-isomer
Hazard and Toxicity: Exp. reprod. effects
RTECS Accession Number: KG3750000
Aldrich: 28577-3
Sigma: E8750
InChi Key: VOXZDWNPVJITMN-UHFFFAOYSA-N
InChi: InChI=1S/C18H24O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6
-7-17(18)20/h3,5,10,14-17,19-20H,2,4,6-9H2,1H3

Derivative: Di-Ac
CRC Number: BBB25-F
CAS Registry Number: 1474-52-8
Molecular Formula: C22H28O4
Molecular Weight: 356.461
Accurate Mass: 356.19876
Percentage Composition: C 74.13%; H 7.92%; O 17.95%
Physical Description: Needles (EtOH aq.)
Melting Point: Mp 139  -  140°     
InChi Key: VQHQLBARMFAKSV-UHFFFAOYSA-N
InChi: InChI=1S/C22H28O4/c1-13(23)25-16-5-7-17-15(12-16)4-6-19-18(17)10-11-22
(3)20(19)8-9-21(22)26-14(2)24/h5,7,12,18-21H,4,6,8-11H2,1-3H3

Variant: 17β-form
Synonym(s): Estradiol, INN,USAN. Oestradiol, BAN. α-Estradiol (obsol., misleading). Almediol. Alora. Climara. Climaval. Compudose. Dermestril. Elleste-solo. Estrace. Estraderm. Evoral. Fermatrix. FemSeven. Menorest. Oestrogel. Ovocyclin. Progynova. Sandrena. Vagifem. Zumenon. Many other names. Evamist.
CRC Number: BBB29-J
CAS Registry Number: 50-28-2
Type of Compound Code(s): XA4130  AJ0100  ZX8000  AJ2350  WA2700  WG9500  VT0100 
Molecular Formula: C18H24O2
Molecular Weight: 272.386
Accurate Mass: 272.17763
Percentage Composition: C 79.37%; H 8.88%; O 11.75%
Biological Source: Isol. from ovaries and pregnancy urine. Sex pheromone for mallard ducks. Present in haemolymph and gonads of various crustaceans, e.g. Homarus americanus, Pandalus kessleri, Parapenaeus fissures and Penaeus monodon
Biological Use / Importance: The most potent of the natural estrogens. Estradiol (and its semisynthetic esters) are used in estrogen replacement therapy
Physical Description: Leaflets or needles (EtOH aq.)
Development Status: Marketed drug. Approved by the FDA (2007) for the treatment of moderate to severe vasomotor symptoms due to menopause
Melting Point: Mp 178°     
Optical Rotation: [α] 18D  +78  ( EtOH)
Partition Coefficient (Calculated): Log P 3.78(uncertain value)(calc)
Hazard and Toxicity: Exp. carcinogen. Human and exp. reprod. effects. Exp. teratogenic effects. Semisynthetic esters should be considered to have similar toxicol. properties
RTECS Accession Number: KG2975000
Aldrich: 25015-5
Fluka: 75262
Sigma: E1132
InChi Key: VOXZDWNPVJITMN-UHFFFAOYSA-N
InChi: InChI=1S/C18H24O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6
-7-17(18)20/h3,5,10,14-17,19-20H,2,4,6-9H2,1H3

Derivative: 17-O-β-D-Glucopyranoside
CRC Number: HGD44-R
CAS Registry Number: 27705-69-7
Type of Compound Code(s): AJ2350  VT0100  AJ0100 
Molecular Formula: C24H34O7
Molecular Weight: 434.528
Accurate Mass: 434.230455
Percentage Composition: C 66.34%; H 7.89%; O 25.77%
Biological Source: Constit. of rabbit urine
Physical Description: Cryst. (EtOH aq.)
Melting Point: Mp 149  -  153°     
Optical Rotation: [α] 25D  -2.7  ( MeOH)
InChi Key: HLORHOWZWQKXIN-UHFFFAOYSA-N
InChi: InChI=1S/C24H34O7/c1-24-9-8-15-14-5-3-13(26)10-12(14)2-4-16(15)17(24)6
-7-19(24)31-23-22(29)21(28)20(27)18(11-25)30-23/h3,5,10,15-23,25-29H,2
,4,6-9,11H2,1H3

Derivative: 3-O-β-D-Glucuronopyranoside
CRC Number: FQY19-K
CAS Registry Number: 15270-30-1
Type of Compound Code(s): AJ0100 
Molecular Formula: C24H32O8
Molecular Weight: 448.512
Accurate Mass: 448.20972
Percentage Composition: C 64.27%; H 7.19%; O 28.54%
Melting Point: Mp 198  -  202°     
Optical Rotation: [α] 24D  -3.9  ( )  ( c, 0.5 in 0.5M NaOH)
InChi Key: MUOHJTRCBBDUOW-UHFFFAOYSA-N
InChi: InChI=1S/C24H32O8/c1-24-9-8-14-13-5-3-12(10-11(13)2-4-15(14)16(24)6-7-
17(24)25)31-23-20(28)18(26)19(27)21(32-23)22(29)30/h3,5,10,14-21,23,25
-28H,2,4,6-9H2,1H3,(H,29,30)

Derivative: 17-O-β-D-Glucuronopyranoside
CRC Number: GNY94-T
CAS Registry Number: 1806-98-0
Type of Compound Code(s): AJ0100 
Molecular Formula: C24H32O8
Molecular Weight: 448.512
Accurate Mass: 448.20972
Percentage Composition: C 64.27%; H 7.19%; O 28.54%
Physical Description: Cryst. (EtOH aq.)
Melting Point: Mp 198  -  202°     
InChi Key: MTKNDAQYHASLID-UHFFFAOYSA-N
InChi: InChI=1S/C24H32O8/c1-24-9-8-14-13-5-3-12(25)10-11(13)2-4-15(14)16(24)6
-7-17(24)31-23-20(28)18(26)19(27)21(32-23)22(29)30/h3,5,10,14-21,23,25
-28H,2,4,6-9H2,1H3,(H,29,30)

Derivative: 17-O-β-D-Glucuronopyranoside, Na salt
CRC Number: GNY95-U
CAS Registry Number: 15087-02-2
Physical Description: Needles (MeOH)
Melting Point: Mp 246  -  250°     
InChi Key: UQSHTUQZFYMYFO-UHFFFAOYSA-M
InChi: InChI=1S/C24H32O8.Na/c1-24-9-8-14-13-5-3-12(25)10-11(13)2-4-15(14)16(2
4)6-7-17(24)31-23-20(28)18(26)19(27)21(32-23)22(29)30;/h3,5,10,14-21,2
3,25-28H,2,4,6-9H2,1H3,(H,29,30);/q;+1/p-1

Derivative: 3-O-Sulfate
CRC Number: BBC63-U
CAS Registry Number: 481-96-9
Extra CAS Registry Numbers(s): 4999-79-5  36083-46-2 
Type of Compound Code(s): XA4130  AJ0100  AJ2350 
Molecular Formula: C18H24O5S
Molecular Weight: 352.451
Accurate Mass: 352.134445
Percentage Composition: C 61.34%; H 6.86%; O 22.70%; S 9.10%
InChi Key: QZIGLSSUDXBTLJ-UHFFFAOYSA-N
InChi: InChI=1S/C18H24O5S/c1-18-9-8-14-13-5-3-12(23-24(20,21)22)10-11(13)2-4-
15(14)16(18)6-7-17(18)19/h3,5,10,14-17,19H,2,4,6-9H2,1H3,(H,20,21,22)

Derivative: Di-Ac
CRC Number: BBB30-D
CAS Registry Number: 3434-88-6
Type of Compound Code(s): AJ0100 
Molecular Formula: C22H28O4
Molecular Weight: 356.461
Accurate Mass: 356.19876
Percentage Composition: C 74.13%; H 7.92%; O 17.95%
Physical Description: Leaflets (MeOH aq.)
Melting Point: Mp 97  -  98°     
Sigma: E0253
InChi Key: VQHQLBARMFAKSV-UHFFFAOYSA-N
InChi: InChI=1S/C22H28O4/c1-13(23)25-16-5-7-17-15(12-16)4-6-19-18(17)10-11-22
(3)20(19)8-9-21(22)26-14(2)24/h5,7,12,18-21H,4,6,8-11H2,1-3H3

Derivative: 17-Propanoyl
Synonym(s): Estradiol monopropionate. Acrofollin. Akrofollin. Follhormon.
CRC Number: BBB33-G
CAS Registry Number: 3758-34-7
Type of Compound Code(s): AJ0100  XA4130  AJ2350 
Molecular Formula: C21H28O3
Molecular Weight: 328.450
Accurate Mass: 328.203845
Percentage Composition: C 76.79%; H 8.59%; O 14.61%
Biological Use / Importance: Estrogen
Melting Point: Mp 199  -  200°     
Partition Coefficient (Calculated): Log P 5.26(uncertain value)(calc)
Sigma: E1758
InChi Key: PQCRZWCSVWBYSC-UHFFFAOYSA-N
InChi: InChI=1S/C21H28O3/c1-3-20(23)24-19-9-8-18-17-6-4-13-12-14(22)5-7-15(13
)16(17)10-11-21(18,19)2/h5,7,12,16-19,22H,3-4,6,8-11H2,1-2H3

Derivative: 3,17-Dipropanoyl
Synonym(s): Estradiol dipropionate, BAN. Agofollin. Diovocyclin. Many other names.
CRC Number: BBB20-A
CAS Registry Number: 113-38-2
Type of Compound Code(s): AJ0100  AJ2350  XA4130 
Molecular Formula: C24H32O4
Molecular Weight: 384.514
Accurate Mass: 384.23006
Percentage Composition: C 74.97%; H 8.39%; O 16.64%
Biological Use / Importance: Estrogen
Physical Description: Leaflets (MeOH aq.)
Melting Point: Mp 104  -  105°     
Partition Coefficient (Calculated): Log P 5.80(uncertain value)(calc)
RTECS Accession Number: KG4725000
Sigma: E9125
InChi Key: JQIYNMYZKRGDFK-UHFFFAOYSA-N
InChi: InChI=1S/C24H32O4/c1-4-22(25)27-16-7-9-17-15(14-16)6-8-19-18(17)12-13-
24(3)20(19)10-11-21(24)28-23(26)5-2/h7,9,14,18-21H,4-6,8,10-13H2,1-3H3

Derivative: 17-Pentanoyl
Synonym(s): Many other names. Estradiol valerate, USAN,INN. Oestradiol valerate, BAN. Atladiol. Deladiol. Delestrogen. Estraval. Progynova. Valergen.
CRC Number: HFH39-G
CAS Registry Number: 979-32-8
Type of Compound Code(s): AJ0100  XA4130  AJ2350 
Molecular Formula: C23H32O3
Molecular Weight: 356.504
Accurate Mass: 356.235145
Percentage Composition: C 77.49%; H 9.05%; O 13.46%
Biological Use / Importance: Estrogen
Development Status: Natazia (estradiol valerate and dienogest) approved by the FDA (May 2010) for the prevention of contraception
Melting Point: Mp 144  -  145°     
Partition Coefficient (Calculated): Log P 6.32(uncertain value)(calc)
RTECS Accession Number: KG5793000
Sigma: E1631
InChi Key: RSEPBGGWRJCQGY-UHFFFAOYSA-N
InChi: InChI=1S/C23H32O3/c1-3-4-5-22(25)26-21-11-10-20-19-8-6-15-14-16(24)7-9
-17(15)18(19)12-13-23(20,21)2/h7,9,14,18-21,24H,3-6,8,10-13H2,1-2H3

Derivative: 17-Heptanoyl
Synonym(s): Estradiol enanthate, USAN,INN. Deladroxate. SQ 16150.
CRC Number: HFW91-N
CAS Registry Number: 4956-37-0
Type of Compound Code(s): AJ2350  AJ0100  XA4130 
Molecular Formula: C25H36O3
Molecular Weight: 384.558
Accurate Mass: 384.266445
Percentage Composition: C 78.08%; H 9.44%; O 12.48%
Biological Use / Importance: Estrogen
Physical Description: Cryst. (diisopropyl ether)
Melting Point: Mp 94  -  96°     
Partition Coefficient (Calculated): Log P 7.37(uncertain value)(calc)
Sigma: E1756
InChi Key: RFWTZQAOOLFXAY-UHFFFAOYSA-N
InChi: InChI=1S/C25H36O3/c1-3-4-5-6-7-24(27)28-23-13-12-22-21-10-8-17-16-18(2
6)9-11-19(17)20(21)14-15-25(22,23)2/h9,11,16,20-23,26H,3-8,10,12-15H2,
1-2H3

Derivative: 3,17-Diheptanoyl
Synonym(s): Estradiol dienanthate.
CRC Number: HFW92-O
CAS Registry Number: 7732-97-0
Type of Compound Code(s): AJ0100  XA4130  AJ2350 
Molecular Formula: C32H48O4
Molecular Weight: 496.729
Accurate Mass: 496.35526
Percentage Composition: C 77.38%; H 9.74%; O 12.88%
Biological Use / Importance: Estrogen
Partition Coefficient (Calculated): Log P 10.04(uncertain value)(calc)
InChi Key: OVAHZPTYWMWNKO-UHFFFAOYSA-N
InChi: InChI=1S/C32H48O4/c1-4-6-8-10-12-30(33)35-24-15-17-25-23(22-24)14-16-2
7-26(25)20-21-32(3)28(27)18-19-29(32)36-31(34)13-11-9-7-5-2/h15,17,22,
26-29H,4-14,16,18-21H2,1-3H3

Derivative: 17-Undecanoyl
Synonym(s): Estradiol undecylate. Delestrec. Depogin. Primogyn-depot. RS 1047. SQ 9993.
CRC Number: HLG15-H
CAS Registry Number: 3571-53-7
Type of Compound Code(s): AJ2350  XA4130  AJ0100 
Molecular Formula: C29H44O3
Molecular Weight: 440.665
Accurate Mass: 440.329045
Percentage Composition: C 79.04%; H 10.06%; O 10.89%
Biological Use / Importance: Estrogen
Partition Coefficient (Calculated): Log P 9.49(uncertain value)(calc)
InChi Key: TXHUMRBWIWWBGW-UHFFFAOYSA-N
InChi: InChI=1S/C29H44O3/c1-3-4-5-6-7-8-9-10-11-28(31)32-27-17-16-26-25-14-12
-21-20-22(30)13-15-23(21)24(25)18-19-29(26,27)2/h13,15,20,24-27,30H,3-
12,14,16-19H2,1-2H3

Derivative: 3,17-Diundecanoyl
Synonym(s): Estradiol diundecylate. Estrolent. Etrosteron. Oestradiol-retard Theramex.
CRC Number: BBB37-K
CAS Registry Number: 1263-57-6
Type of Compound Code(s): AJ2350  XA4130  AJ0100 
Molecular Formula: C40H64O4
Molecular Weight: 608.943
Accurate Mass: 608.48046
Percentage Composition: C 78.90%; H 10.59%; O 10.51%
Biological Use / Importance: Estrogen
Partition Coefficient (Calculated): Log P 14.27(uncertain value)(calc)
InChi Key: PWQIMJUJIMPDSQ-UHFFFAOYSA-N
InChi: InChI=1S/C40H64O4/c1-4-6-8-10-12-14-16-18-20-38(41)43-32-23-25-33-31(3
0-32)22-24-35-34(33)28-29-40(3)36(35)26-27-37(40)44-39(42)21-19-17-15-
13-11-9-7-5-2/h23,25,30,34-37H,4-22,24,26-29H2,1-3H3

Derivative: 3,17-Bis(10-undecenoyl)
Synonym(s): Estradiol diundecylenate.
CRC Number: BBB38-L
CAS Registry Number: 74798-17-7
Type of Compound Code(s): XA4130  AJ2350  AJ0100 
Molecular Formula: C40H60O4
Molecular Weight: 604.912
Accurate Mass: 604.44916
Percentage Composition: C 79.42%; H 10.00%; O 10.58%
Biological Use / Importance: Estrogen
Partition Coefficient (Calculated): Log P 13.30(uncertain value)(calc)
InChi Key: LVJFPCSLAMHGAU-UHFFFAOYSA-N
InChi: InChI=1S/C40H60O4/c1-4-6-8-10-12-14-16-18-20-38(41)43-32-23-25-33-31(3
0-32)22-24-35-34(33)28-29-40(3)36(35)26-27-37(40)44-39(42)21-19-17-15-
13-11-9-7-5-2/h4-5,23,25,30,34-37H,1-2,6-22,24,26-29H2,3H3

Derivative: 17-Hexadecanoyl
Synonym(s): Estradiol palmitate. Esmopal.
CRC Number: BBB23-D
CAS Registry Number: 5776-45-4
Type of Compound Code(s): AJ2350  AJ0100  XA4130 
Molecular Formula: C34H54O3
Molecular Weight: 510.799
Accurate Mass: 510.407295
Percentage Composition: C 79.95%; H 10.66%; O 9.40%
Biological Use / Importance: Estrogen
Melting Point: Mp 69  -  71°     
Partition Coefficient (Calculated): Log P 12.14(uncertain value)(calc)
InChi Key: XQKLZLWOOGGXMV-UHFFFAOYSA-N
InChi: InChI=1S/C34H54O3/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-33(36)37-32-22
-21-31-30-19-17-26-25-27(35)18-20-28(26)29(30)23-24-34(31,32)2/h18,20,
25,29-32,35H,3-17,19,21-24H2,1-2H3

Derivative: 17-Octadecanoyl
Synonym(s): Estradiol stearate. Depofollan.
CRC Number: HGD46-T
CAS Registry Number: 82205-00-3
Type of Compound Code(s): XA4130  AJ0100  AJ2350 
Molecular Formula: C36H58O3
Molecular Weight: 538.852
Accurate Mass: 538.438595
Percentage Composition: C 80.24%; H 10.85%; O 8.91%
Biological Use / Importance: Estrogen
Melting Point: Mp 78  -  79°     
Partition Coefficient (Calculated): Log P 13.19(uncertain value)(calc)
InChi Key: KIADYVOYCQRXRE-UHFFFAOYSA-N
InChi: InChI=1S/C36H58O3/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-35(38)39
-34-24-23-33-32-21-19-28-27-29(37)20-22-30(28)31(32)25-26-36(33,34)2/h
20,22,27,31-34,37H,3-19,21,23-26H2,1-2H3

Derivative: 17-(2,2-Dimethylpropanoyl)
Synonym(s): Estradiol pivalate. Estradiol trimethylacetate. Estrotate.
CRC Number: HLG14-G
CAS Registry Number: 24894-50-6
Type of Compound Code(s): AJ2350  AJ0100  XA4130 
Molecular Formula: C23H32O3
Molecular Weight: 356.504
Accurate Mass: 356.235145
Percentage Composition: C 77.49%; H 9.05%; O 13.46%
Biological Use / Importance: Estrogen
Melting Point: Mp 229  -  231°     
Partition Coefficient (Calculated): Log P 5.97(uncertain value)(calc)
InChi Key: SLOFBKMZOOTTDZ-UHFFFAOYSA-N
InChi: InChI=1S/C23H32O3/c1-22(2,3)21(25)26-20-10-9-19-18-7-5-14-13-15(24)6-8
-16(14)17(18)11-12-23(19,20)4/h6,8,13,17-20,24H,5,7,9-12H2,1-4H3

Derivative: 17-(3-Carboxypropanoyl)
Synonym(s): Estradiol hemisuccinate. Eutocol.
CRC Number: BBB32-F
CAS Registry Number: 7698-93-3
Type of Compound Code(s): AJ0100  AJ2350  XA4130 
Molecular Formula: C22H28O5
Molecular Weight: 372.460
Accurate Mass: 372.193675
Percentage Composition: C 70.95%; H 7.58%; O 21.48%
Biological Use / Importance: Estrogen
Physical Description: Dimorphic shiny cryst. (C6H6)
Melting Point: Mp 145  -  147°      Mp 163°     
Partition Coefficient (Calculated): Log P 4.47(uncertain value)(calc)
Sigma: E9252
InChi Key: YJPIDPAGJSWWBE-UHFFFAOYSA-N
InChi: InChI=1S/C22H28O5/c1-22-11-10-16-15-5-3-14(23)12-13(15)2-4-17(16)18(22
)6-7-19(22)27-21(26)9-8-20(24)25/h3,5,12,16-19,23H,2,4,6-11H2,1H3,(H,2
4,25)

Derivative: 17-(Butanoylacetyl)
Synonym(s): Estra-1,3,5(10)-triene-3,17-diol 17-(3-oxohexanoate), 9CI. Estradiol butyrylacetate. Follikoside.
CRC Number: HLG13-F
CAS Registry Number: 60883-80-9
Type of Compound Code(s): AJ2350  XA4130  AJ0100 
Molecular Formula: C24H32O4
Molecular Weight: 384.514
Accurate Mass: 384.23006
Percentage Composition: C 74.97%; H 8.39%; O 16.64%
Biological Use / Importance: Estrogen
Partition Coefficient (Calculated): Log P 5.41(uncertain value)(calc)
InChi Key: LLWMXKOTHFASEO-UHFFFAOYSA-N
InChi: InChI=1S/C24H32O4/c1-3-4-16(25)14-23(27)28-22-10-9-21-20-7-5-15-13-17(
26)6-8-18(15)19(20)11-12-24(21,22)2/h6,8,13,19-22,26H,3-5,7,9-12,14H2,
1-2H3

Derivative: 17-(3-Cyclopentylpropanoyl)
Synonym(s): Estradiol cypionate, INN. Depofemin. Estradep. Many other names.
CRC Number: HLG12-E
CAS Registry Number: 313-06-4
Type of Compound Code(s): XA4130  AJ2350  AJ0100 
Molecular Formula: C26H36O3
Molecular Weight: 396.569
Accurate Mass: 396.266445
Percentage Composition: C 78.75%; H 9.15%; O 12.10%
Biological Use / Importance: Estrogen
Physical Description: Cryst. (C6H6/petrol)
Melting Point: Mp 151  -  152°     
Optical Rotation: [α] 25D  +45  ( CHCl3)
Partition Coefficient (Calculated): Log P 7.35(uncertain value)(calc)
Other Data: Component of Depo-Testadiol
Hazard and Toxicity: Exp. reprod. and teratogenic effects
RTECS Accession Number: KG4600000
Sigma: E8004
InChi Key: UOACKFBJUYNSLK-UHFFFAOYSA-N
InChi: InChI=1S/C26H36O3/c1-26-15-14-21-20-10-8-19(27)16-18(20)7-9-22(21)23(2
6)11-12-24(26)29-25(28)13-6-17-4-2-3-5-17/h8,10,16-17,21-24,27H,2-7,9,
11-15H2,1H3

Derivative: 17-Cyclohexanecarboxylate
Synonym(s): Estradiol hexahydrobenzoate, INN. Benzo-Ginoestril A.P.. Benzo-Gynoestryl retard. Ginestryl-15-depot. Menodin‡. Tardoginestryl.
CRC Number: BSV52-W
CAS Registry Number: 15140-27-9
Type of Compound Code(s): AJ2350  XA4130  AJ0100 
Molecular Formula: C25H34O3
Molecular Weight: 382.542
Accurate Mass: 382.250795
Percentage Composition: C 78.49%; H 8.96%; O 12.55%
Biological Use / Importance: Estrogen
Melting Point: Mp 91  -  92°     
Optical Rotation: [α] 20D  +53  ( c, 1 in CHCl3)
Partition Coefficient (Calculated): Log P 6.76(uncertain value)(calc)
InChi Key: IVRCALGRJCHPRV-UHFFFAOYSA-N
InChi: InChI=1S/C25H34O3/c1-25-14-13-20-19-10-8-18(26)15-17(19)7-9-21(20)22(2
5)11-12-23(25)28-24(27)16-5-3-2-4-6-16/h8,10,15-16,20-23,26H,2-7,9,11-
14H2,1H3

Derivative: 3-Benzoyl
Synonym(s): Oestradiol benzoate, BAN. Estradiol benzoate, INN. Benovocyclin. Benzofoline. Many other names.
CRC Number: BBB31-E
CAS Registry Number: 50-50-0
Type of Compound Code(s): AJ0100  XA4130  AJ2350 
Molecular Formula: C25H28O3
Molecular Weight: 376.494
Accurate Mass: 376.203845
Percentage Composition: C 79.76%; H 7.50%; O 12.75%
Biological Use / Importance: Estrogen
Physical Description: Cryst. (MeOH aq.)
Melting Point: Mp 193°     
Optical Rotation: [α] 25D  +58  ( c, 2 in dioxan)
Partition Coefficient (Calculated): Log P 5.93(uncertain value)(calc)
Other Data: Component of Mixogen and Synovex
RTECS Accession Number: KG4050000
Aldrich: 28578-1
Fluka: 75270
Sigma: E8515
InChi Key: UYIFTLBWAOGQBI-UHFFFAOYSA-N
InChi: InChI=1S/C25H28O3/c1-25-14-13-20-19-10-8-18(28-24(27)16-5-3-2-4-6-16)1
5-17(19)7-9-21(20)22(25)11-12-23(25)26/h2-6,8,10,15,20-23,26H,7,9,11-1
4H2,1H3

Derivative: 3-Benzoyl, 17-[[4-[4-[bis(2-chloroethyl)amino]phenyl]-1-oxobutoxy]acetyl]
Synonym(s): Atrimustine, INN. Bestrabucil. Busramustine. KM 2210.
CRC Number: HGD45-S
CAS Registry Number: 75219-46-4
Type of Compound Code(s): AJ0100  AJ3050  XA1950  AJ2350 
Molecular Formula: C41H47Cl2NO6
Molecular Weight: 720.731
Accurate Mass: 719.278043
Percentage Composition: C 68.33%; H 6.57%; Cl 9.84%; N 1.94%; O 13.32%
Biological Use / Importance: Antineoplastic agent
Physical Description: Cryst.
Partition Coefficient (Calculated): Log P 10.46(uncertain value)(calc)
Hazard and Toxicity: Exp. reprod. and teratogenic effects
RTECS Accession Number: KG7200000
InChi Key: IFJUINDAXYAPTO-UHFFFAOYSA-N
InChi: InChI=1S/C41H47Cl2NO6/c1-41-21-20-34-33-17-15-32(49-40(47)29-7-3-2-4-8
-29)26-30(33)12-16-35(34)36(41)18-19-37(41)50-39(46)27-48-38(45)9-5-6-
28-10-13-31(14-11-28)44(24-22-42)25-23-43/h2-4,7-8,10-11,13-15,17,26,3
4-37H,5-6,9,12,16,18-25,27H2,1H3

Derivative: O17-(3-Pyridinecarboxylate), 3-propanoyl
Synonym(s): Estrapronicate, INN.
CRC Number: BBN32-N
CAS Registry Number: 4140-20-9
Type of Compound Code(s): XA4130  AJ2350  AJ0100  AJ2450 
Molecular Formula: C27H31NO4
Molecular Weight: 433.546
Accurate Mass: 433.225309
Percentage Composition: C 74.80%; H 7.21%; N 3.23%; O 14.76%
Biological Use / Importance: Anabolic agent. Estrogen
Physical Description: Cryst. (EtOH)
Melting Point: Mp 122  -  123°     
Partition Coefficient (Calculated): Log P 5.86(uncertain value)(calc)
InChi Key: FXMSQUVSUXBBAB-UHFFFAOYSA-N
InChi: InChI=1S/C27H31NO4/c1-3-25(29)31-19-7-9-20-17(15-19)6-8-22-21(20)12-13
-27(2)23(22)10-11-24(27)32-26(30)18-5-4-14-28-16-18/h4-5,7,9,14-16,21-
24H,3,6,8,10-13H2,1-2H3

Derivative: 17-(2-Furancarbonyl)
Synonym(s): Estradiol furoate. Di-folliculine.
CRC Number: BSV54-Y
Type of Compound Code(s): XA4130  AJ0100  AJ2350 
Molecular Formula: C23H26O4
Molecular Weight: 366.456
Accurate Mass: 366.18311
Percentage Composition: C 75.39%; H 7.15%; O 17.46%
Biological Use / Importance: Estrogen
Partition Coefficient (Calculated): Log P 5.84(uncertain value)(calc)
InChi Key: UZMCMLLMBRERNY-UHFFFAOYSA-N
InChi: InChI=1S/C23H26O4/c1-23-11-10-17-16-7-5-15(24)13-14(16)4-6-18(17)19(23
)8-9-21(23)27-22(25)20-3-2-12-26-20/h2-3,5,7,12-13,17-19,21,24H,4,6,8-
11H2,1H3

Derivative: 17-[3-(4-Propoxyphenyl)propanoyl]
Synonym(s): Estradiol propoxyphenylpropionate. Estradiol p-propoxyhydrocinnamate. Durovex.
CRC Number: BBB40-G
CAS Registry Number: 7724-88-1
Type of Compound Code(s): AJ0100  XA4130  AJ2350 
Molecular Formula: C30H38O4
Molecular Weight: 462.628
Accurate Mass: 462.27701
Percentage Composition: C 77.89%; H 8.28%; O 13.83%
Biological Use / Importance: Estrogen
Physical Description: Cryst. (MeOH aq.)
Melting Point: Mp 126  -  128°     
Optical Rotation: [α] D  +48  ( c, 1 in dioxan)
Partition Coefficient (Calculated): Log P 7.65(uncertain value)(calc)
InChi Key: JNWIUSBBFNMZRQ-UHFFFAOYSA-N
InChi: InChI=1S/C30H38O4/c1-3-18-33-23-9-4-20(5-10-23)6-15-29(32)34-28-14-13-
27-26-11-7-21-19-22(31)8-12-24(21)25(26)16-17-30(27,28)2/h4-5,8-10,12,
19,25-28,31H,3,6-7,11,13-18H2,1-2H3

Derivative: 3,17-Bis[4-[bis(2-chloroethyl)amino]phenylacetyl]
Synonym(s): Estradiol mustard. Chlorphenacyl estradiol diester. NSC 112259.
CRC Number: BBB41-H
CAS Registry Number: 22966-79-6
Type of Compound Code(s): AJ3050  AJ0100  XA1950 
Molecular Formula: C42H50Cl4N2O4
Molecular Weight: 788.679
Accurate Mass: 786.252466
Percentage Composition: C 63.96%; H 6.39%; Cl 17.98%; N 3.55%; O 8.11%
Biological Use / Importance: Antineoplastic agent
Physical Description: No phys. props. reported
Partition Coefficient (Calculated): Log P 10.67(uncertain value)(calc)
Hazard and Toxicity: Exp. carcinogen
RTECS Accession Number: KG7300000
InChi Key: LRSFXIJGHRPOQQ-UHFFFAOYSA-N
InChi: InChI=1S/C42H50Cl4N2O4/c1-42-17-16-36-35-13-11-34(51-40(49)26-29-2-7-3
2(8-3-29)47(22-18-43)23-19-44)28-31(35)6-12-37(36)38(42)14-15-39(42)52
-41(50)27-30-4-9-33(10-5-30)48(24-20-45)25-21-46/h2-5,7-11,13,28,36-39
H,6,12,14-27H2,1H3

Derivative: 3-Bis(2-chloroethyl)carbamate
See Estramustine
CRC Number: HLG21-G

Derivative: Chloral hemiacetal
See Cloxestradiol
CRC Number: BBB43-J

Derivative: 3-Me ether
Synonym(s): 3-O-Methylestradiol.
CRC Number: NQG75-W
CAS Registry Number: 1035-77-4
Type of Compound Code(s): AJ0100 
Molecular Formula: C19H26O2
Molecular Weight: 286.413
Accurate Mass: 286.19328
Percentage Composition: C 79.68%; H 9.15%; O 11.17%
Physical Description: Prisms (MeOH)
Melting Point: Mp 96  -  98°     
Optical Rotation: [α] D  +72.3 
Sigma: E9250
InChi Key: ULAADVBNYHGIBP-UHFFFAOYSA-N
InChi: InChI=1S/C19H26O2/c1-19-10-9-15-14-6-4-13(21-2)11-12(14)3-5-16(15)17(1
9)7-8-18(19)20/h4,6,11,15-18,20H,3,5,7-10H2,1-2H3

Derivative: 3-Me ether, phenylcarbamate
Synonym(s): STS 153.
CRC Number: NQG76-X
CAS Registry Number: 43085-16-1
Type of Compound Code(s): AJ0100 
Molecular Formula: C26H31NO3
Molecular Weight: 405.536
Accurate Mass: 405.230394
Percentage Composition: C 77.01%; H 7.70%; N 3.45%; O 11.84%
Biological Use / Importance: Colpotropic and uterotropic agent
InChi Key: PQMLUQDWRKGALJ-UHFFFAOYSA-N
InChi: InChI=1S/C26H31NO3/c1-26-15-14-21-20-11-9-19(29-2)16-17(20)8-10-22(21)
23(26)12-13-24(26)30-25(28)27-18-6-4-3-5-7-18/h3-7,9,11,16,21-24H,8,10
,12-15H2,1-2H3,(H,27,28)

Derivative: 17-(1-Cyclohexenyl) ether, 3-propanoyl
See Orestrate
CRC Number: BBB22-C

Variant: (8α,17β)-form
Synonym(s): Isoestradiol.
CRC Number: OGV19-Y
CAS Registry Number: 517-04-4
Type of Compound Code(s): AJ0100 
Molecular Formula: C18H24O2
Molecular Weight: 272.386
Accurate Mass: 272.17763
Percentage Composition: C 79.37%; H 8.88%; O 11.75%
Physical Description: Cryst. (MeOH/CHCl3)
Melting Point: Mp 181°     
Optical Rotation: [α] 20D  +9.5  ( c, 0.85 in dioxan)
Other Data: Possess ca. 0.5 the estrogenic activity of estradiol
InChi Key: VOXZDWNPVJITMN-UHFFFAOYSA-N
InChi: InChI=1S/C18H24O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6
-7-17(18)20/h3,5,10,14-17,19-20H,2,4,6-9H2,1H3

References:
Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 1055C  (ir)
Aldrich Library of 13C and 1H FT-NMR Spectra, 1992, 3, 565A; 589B; 3, 600B  (nmr)
Miescher, K.  et al., Helv. Chim. Acta, 1937, 20, 263- 271; 1237- 1244  (esters, props)
Miescher, K.  et al., Biochem. J., 1938, 32, 1273- 1280  (esters, props)
Marker, R.E.JACS, 1938, 60, 2927- 2928  (Estradiol, synth)
US Pat., 1952, 2 611 773  (cypionate, synth, activity)
Junkmann, K.Arch. Exp. Pathol. Pharmakol., 1953, 220, 378- 390  (esters, pharmacol)
Diczfalusy, E.  et al., Endocrinology (Baltimore), 1954, 54, 471- 477  (polymer)
Ferno, O.  et al., Acta Chem. Scand., 1958, 12, 1675- 1689  (polymer, synth)
Gauthier, B.  et al., Ann. Pharm. Fr., 1958, 16, 757- 766  (enanthate, synth)
US Pat., 1958, 2 842 567; () , 2 846 455  (oxohexanoate, hexahydrobenzoate)
Wotiz, H.H.  et al., JACS, 1959, 81, 1704- 1708  (glucuronopyranosyl, synth)
Wolff, M.E.  et al., JOC, 1959, 24, 1612- 1613  (enanthate, synth)
Diczfalusy, E.  et al., Acta Chem. Scand., 1963, 17, 2536- 2547  (propoxyhydrocinnamate, activity)
Miki, T.  et al., Proc. Chem. Soc., London, 1963, 139  (Estradiol, synth)
Ohrt, J.M.  et al., Acta Cryst., 1964, 17, 1611  (cryst struct, derivs)
Gauthier, B.  et al., Ann. Pharm. Fr., 1966, 24, 101- 107  (Estrapronicate, synth)
Gibian, H.  et al., Tet. Lett., 1966, 7, 2321- 2330  (3-Me ether, synth)
Savini, E.C.  et al., Therapie, 1966, 21, 81- 98  (Estrapronicate, activity)
Tsukuda, Y.  et al., JCS(B), 1968, 1387- 1393  (Estradiol 3-(4-bromobenzoate), cryst struct)
Williamson, D.G.Biochemistry, 1969, 8, 4299- 4304  (glucoside, synth)
Wall, M.E.  et al., J. Med. Chem., 1969, 12, 810- 818  (Estradiol, mustard, activity)
US Pat., 1969, 3 471 479  (pivalate, synth)
Yellin, T.O.J. Lipid Res., 1972, 13, 554- 555  (succinate, synth)
Vollmer, E.P.  et al., Cancer Chemother. Rep., Part 3, 1973, 4, 121- 140  (Estradiol, mustard, rev)
Wittstruck, T.A.  et al., JOC, 1973, 38, 1542- 1548  (cmr)
Ponsold, K.  et al., Pharmazie, 1973, 28, 371- 376; 1977, 32, 598- 602; 1979, 34, 250  (3-Me ether, STS 153)
Florey, K.Anal. Profiles Drug Subst., 1975, 4, 192- 208  (valerate, rev)
Busetta, B.  et al., Acta Cryst. B, 1976, 32, 1290- 1292  (17α-form, cryst struct)
Eder, U.  et al., Chem. Ber., 1976, 109, 2948- 2953  (Estradiol, synth)
Nishino, Y.  et al., Steroids, 1976, 28, 325- 337  (Estradiol, biol, sar)
Kametani, T.  et al., JACS, 1978, 100, 6218- 6220  (3-Me ether, synth, ir, pmr)
Cronholm, T.  et al., Eur. J. Biochem., 1979, 96, 605- 611  (sulfate, synth)
IARC Monogr., 1979, 21, 279- 326  (Estradiol esters, tox, rev)
Oriowo, M.A.  et al., Contraception, 1980, 21, 415- 424  (cypionate, valerate, activity)
Ger. Pat., 1980, 2 932 607  (Atrimustine, manuf)
Quinkert, G.  et al., Annalen, 1981, 2335- 2371; 1982, , 1999- 2040  (17β-form, synth)
Liehr, J.G.  et al., Steroids, 1982, 39, 599- 605  (sulfate, ms)
Numazawa, M.  et al., JCS Perkin 1, 1983, 121- 125  (glucuronopyranosyl, struct)
Hylarides, M.D.  et al., JOC, 1984, 49, 2744- 2745  (Estradiol, synth)
Oketani, Y.  et al., Oyo Yakuri, 1984, 27, 87- 93; 28, 315- 327; 1984, 27, 95- 102; 1984, 27, 103- 106; 1984, 27, 107- 115  (Atrimustine, activity)
Larner, J.M.  et al., Endocrinology (Baltimore), 1985, 117, 1209- 1214  (Estradiol, metab)
Salole, E.G.  et al., Anal. Profiles Drug Subst., 1986, 15, 283- 318  (Estradiol, rev)
Reck, G.  et al., Cryst. Res. Technol., 1986, 21, 1313- 1319  (3-Me ether, cryst struct)
Couch, E.F.  et al., Comp. Biochem. Physiol., A: Physiol., 1987, 87, 765- 770  (Estradiol, occur, lobster)
Schneider, G.  et al., Annalen, 1988, 679- 683  (3-Me ether, synth, pmr, cmr, ir)
Bohnet, S.  et al., J. Biol. Chem., 1991, 266, 9795- 9804  (Estradiol, pheromone)
Negwer, M.Organic-Chemical Drugs and their Synonyms, 7th edn., Akademie-Verlag, 1994, 6627  (synonyms)
Diomme, P.  et al., Steroids, 1995, 60, 830- 836  (sulfate, cmr)
Collins, M.A.  et al., Tet. Lett., 1995, 36, 4467- 4470  (Estradiol, synth)
Bolaños-Garcia, V.M.  et al., Acta Cryst. C, 1996, 52, 1997- 2000  (estradiol benzoate, cryst struct)
Werschkun, B.  et al., J. Carbohydr. Chem., 1999, 18, 629- 637  (Estradiol, glucuronide, synth)
Rigby, J.H.  et al., JACS, 1999, 121, 8237- 8245  (17β-form, synth)
Martindale, The Complete Drug Reference, 32nd edn., Pharmaceutical Press, 1999, 1455
Merck Index, 13th edn., 2001, 5185  (isoestradiol, props, bibl)
Wellington, K.  et al., Drugs, 2002, 62, 491- 504  (estradiol valerate, rev)
Parrish, D.A.  et al., Acta Cryst. C, 2003, 59, o80- o82  (17β-form, cryst struct)
Chiechi, L.M.IDrugs, 2004, 7, 860- 864  (rev)
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Guo, J.  et al., Tet. Lett., 2010, 51, 3465- 3469  (17α, 17β-forms, conformn)
Sax's Dangerous Properties of Industrial Materials, 11th edn., J. Wiley, 2004, BFV325; , EDO000; , EDP000; , EDR000; , EDS100; , DAZ115; , EDO500; , EDR500


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