InChI=1/C12H20O2/c1-6-14-11(13)10-9(7-8(2)3)12(10,4)5/h7,9-10H,6H2,1-5H3

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Inherent Properties, Identifiers and References

ChemSpider ID:	7057
Empirical Formula:	C₁₂H₂₀O₂
Molecular Weight:	196.286
Nominal Mass:	196 Da
Average Mass:	196.286 Da
Monoisotopic Mass:	196.14633 Da

Systematic Name:

ethyl 2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate

SMILES:

O=C(OCC)C1C(/C=C(/C)C)C1(C)C

InChI:

InChI=1/C12H20O2/c1-6-14-11(13)10-9(7-8(2)3)12(10,4)5/h7,9-10H,6H2,1-5H3

InChIKey:

VIMXTGUGWLAOFZ-UHFFFAOYAX

Associated Data Sources and Commercial Suppliers

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Supplemental Information

User Data

miscellaneous

Source: pyrethrum flowers

No description available

Source: constituent of pyrethrum flowers

No description available

Drug Status: experimental

No description available

Chemical Class: terpene

No description available

Names and Synonyms

Validated by Experts, Validated by Users, Non-Validated, Removed by Users, Redirected by Users, Redirect Approved by Experts

Cyclopropanecarboxylic acid, 2,2-dimethyl-3- (2-methylpropenyl)-, ethyl ester

Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methylpropenyl)-, ethyl ester (8CI)

Ethyl 2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate

ethyl chrysanthemate

2,2-Dimethyl-3-(1-isobutenyl)cyclopropane-1-carboxylic acid ethyl ester

2,2-Dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylic acid ethyl ester

202-579-7 [EINECS/ELINCS]

4-09-00-00170 (Beilstein Handbook Reference) [Beilstein]

97-41-6 [RN]

Chrysanthemic acid ethyl ester

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Database ID(s)

Validated by Experts, Validated by Users, Non-Validated, Removed by Users, Redirected by Users, Redirect Approved by Experts

Predicted Properties

LogP:	ACD/LogP: 4.26 XLogP: 3.30	# of Rule of 5 Violations:	0
ACD/LogD (pH 5.5):	4.26	ACD/LogD (pH 7.4):	4.26
ACD/BCF (pH 5.5):	1017.13	ACD/BCF (pH 7.4):	1017.13
ACD/KOC (pH 5.5):	4946.28	ACD/KOC (pH 7.4):	4946.28
#H bond acceptors:	2	#H bond donors:	0
#Freely Rotating Bonds:	4	Polar Surface Area:	26.3 Å²
Index of Refraction:	1.507	Molar Refractivity:	58.96 cm³
Molar Volume:	197.9 cm³	Polarizability:	23.37 10^-24cm³
Surface Tension:	35.3 dyne/cm	Density:	0.991 g/cm³
Flash Point:	84.4 °C	Enthalpy of Vaporization:	47.78 kJ/mol
Boiling Point:	240.8 °C at 760 mmHg	Vapour Pressure:	0.0372 mmHg at 25°C

MeSH

EPI Summary

            
 Log Octanol-Water Partition Coef (SRC):
    Log Kow (KOWWIN v1.67 estimate) =  4.26

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  231.48  (Adapted Stein & Brown method)
    Melting Pt (deg C):  14.99  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  0.0724  (Mean VP of Antoine & Grain methods)
    BP  (exp database):  112 @ 10 mm Hg deg C

 Water Solubility Estimate from Log Kow (WSKOW v1.41):
    Water Solubility at 25 deg C (mg/L):  10.44
       log Kow used: 4.26 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  40.822 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Esters

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.03E-003  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.791E-003 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  4.26  (KowWin est)
  Log Kaw used:  -1.376  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  5.636
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.6443
   Biowin2 (Non-Linear Model)     :   0.9294
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.6935  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.6401  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.6221
   Biowin6 (MITI Non-Linear Model):   0.5001
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.3072
 Ready Biodegradability Prediction:   NO

Hydrocarbon Biodegradation (BioHCwin v1.01):
    Structure incompatible with current estimation method!

 Sorption to aerosols (25 Dec C)[AEROWIN v1.00]:
  Vapor pressure (liquid/subcooled):  9.12 Pa (0.0684 mm Hg)
  Log Koa (Koawin est  ): 5.636
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  3.29E-007 
       Octanol/air (Koa) model:  1.06E-007 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  1.19E-005 
       Mackay model           :  2.63E-005 
       Octanol/air (Koa) model:  8.49E-006 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  89.2451 E-12 cm3/molecule-sec
      Half-Life =     0.120 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.438 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =    43.000000 E-17 cm3/molecule-sec
      Half-Life =     0.027 Days (at 7E11 mol/cm3)
      Half-Life =     38.378 Min
   Reaction With Nitrate Radicals May Be Important!
   Fraction sorbed to airborne particulates (phi): 1.91E-005 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  527
      Log Koc:  2.722 

 Aqueous Base/Acid-Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:
  Total Kb for pH > 8 at 25 deg C :  1.201E-002  L/mol-sec
  Kb Half-Life at pH 8:       1.829  years  
  Kb Half-Life at pH 7:      18.293  years  

 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = 0.933 (BCF = 8.571)
       log Kow used: 4.26 (estimated)

 Volatilization from Water:
    Henry LC:  0.00103 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River:      2.226  hours
    Half-Life from Model Lake :      141.8  hours   (5.907 days)

 Removal In Wastewater Treatment:
    Total removal:              56.52  percent
    Total biodegradation:        0.34  percent
    Total sludge adsorption:    38.46  percent
    Total to Air:               17.72  percent
      (using 10000 hr Bio P,A,S)

 Level III Fugacity Model:
           Mass Amount    Half-Life    Emissions
            (percent)        (hr)       (kg/hr)
   Air       0.0421          0.523        1000       
   Water     9.35            900          1000       
   Soil      86.6            1.8e+003     1000       
   Sediment  4.04            8.1e+003     0          
     Persistence Time: 939 hr

SimBioSys LASSO

Descriptors: 0, 0, 0, 0, 0, 0, 0, 2, 1, 0, 0, 0, 17, 0, 2, 1, 0, 2, 1, 0, 2, 0, 0, 0

Category	Target	PDB Code	LASSO Score
Nuclear Hormone Receptors	GR, glucocorticoid receptor	1m2z	0.08
Other Enzymes	HMGR, hydroxymethylglutaryl-CoA reductase	1hw8	0.07
Metalloenzymes	ACE, angiotensin-converting enzyme	1o86	0.03
Nuclear Hormone Receptors	PPARg, peroxisome proliferator activated receptor	1fm9	0.03
Nuclear Hormone Receptors	RXRa, retinoic X receptor R	1mvc	0.02
Kinases	SRC, tyrosine kinase SRC	2src	0.01
Other Enzymes	HIVPR, HIV protease	1hpx	0.01
Serine Proteases	Thrombin	1ba8	0.01
Metalloenzymes	PDE5, phosphodiesterase 5	1xp0	0.01
Nuclear Hormone Receptors	MR, mineralocorticoid receptor	2aa2	0.01
Other Enzymes	PARP, poly(ADP-ribose) polymerase	1efy	0.01
Other Enzymes	PNP, purine nucleoside phosphorylase	1b8o	0.00
Nuclear Hormone Receptors	AR, androgen receptor	1xq2	0.00
Other Enzymes	AmpC, AmpC beta-lactamase	1xgj	0.00
Nuclear Hormone Receptors	ER, estrogen receptor; agonist	1l2i	0.00
Folate Enzymes	DHFR, dihydrofolate reductase	3dfr	0.00
Nuclear Hormone Receptors	PR, progesterone receptor	1sr7	0.00
Other Enzymes	HIVRT, HIV reverse transcriptase	1rt1	0.00
Kinases	VEGFr2, vascular endothelial growth factor receptor	1vr2	0.00
Other Enzymes	GPB, glycogen phosphorylase	1a8i	0.00
Other Enzymes	NA, neuraminidase	1a4g	0.00
Kinases	FGFr1, fibroblast growth factor receptor kinase	1agw	0.00
Other Enzymes	SAHH, S-adenosyl-homocysteine hydrolase	1a7a	0.00
Other Enzymes	InhA, enoyl ACP reductase	1p44	0.00
Other Enzymes	COX-2, cyclooxygenase-2	1cx2	0.00
Other Enzymes	ALR2, aldose reductase	1ah3	0.00
Metalloenzymes	COMT, catechol O-methyltransferase	1h1d	0.00
Kinases	CDK2, cyclindependent kinase 2	1ckp	0.00
Kinases	TK, thymidine kinase	1kim	0.00
Kinases	P38 MAP, P38 mitogen activated protein	1kv2	0.00
Kinases	PDGFrb, platelet derived growth factor receptor kinase	N/A	0.00
Folate Enzymes	GART, glycinamide ribonucleotide transformylase	1c2t	0.00
Kinases	HSP90, human heat shock protein 90	1uy6	0.00
Serine Proteases	FXa, factor Xa	1f0r	0.00
Kinases	EGFr, epidermal growth factor receptor	1m17	0.00
Other Enzymes	AChE, acetylcholinesterase	1eve	0.00
Metalloenzymes	ADA, adenosine deaminase	1stw	0.00