NP-MRD: Showing NP-Card for (1s,2s,5s,8s)-2,6-dimethyl-9-(propan-2-ylidene)-11-oxatricyclo[6.2.1.0¹,⁵]undec-6-en-8-ol (NP0147227)

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Record Information

Version

2.0

Created at

2022-09-02 02:47:20 UTC

Updated at

2022-09-02 02:47:20 UTC

NP-MRD ID

NP0147227

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2s,5s,8s)-2,6-dimethyl-9-(propan-2-ylidene)-11-oxatricyclo[6.2.1.0¹,⁵]undec-6-en-8-ol

Description

Curcumenol belongs to the class of organic compounds known as guaianes. These are sesquiterpenoids with a structure based on the guaiane skeleton. Guaiane is a bicyclic compound consisting of a decahydroazulene moiety, substituted with two methyl groups and a 1-methylethyl group at the 1-, 4-, and 7-position, respectively. (1s,2s,5s,8s)-2,6-dimethyl-9-(propan-2-ylidene)-11-oxatricyclo[6.2.1.0¹,⁵]undec-6-en-8-ol is found in Curcuma phaeocaulis. (1s,2s,5s,8s)-2,6-dimethyl-9-(propan-2-ylidene)-11-oxatricyclo[6.2.1.0¹,⁵]undec-6-en-8-ol was first documented in 2022 (PMID: 36016561). Based on a literature review a small amount of articles have been published on Curcumenol (PMID: 35795557) (PMID: 35795276) (PMID: 35718518).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          2D

 39 41  0  0  0  0  0  0  0  0999 V2000
    4.1443   -0.0855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6443   -0.0855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8943    1.2135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3943    1.2135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8578    2.6401    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2760    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3943   -1.2135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0323   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0323    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2458    1.6317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0890    3.1235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6161    1.0216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2182   -2.5795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1105   -3.7852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8876   -3.5930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1932   -2.8545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8943   -1.3846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6443   -0.0855    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1443    1.4145    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3271   -1.5743    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6443    2.5126    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0025    3.8689    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2918   -1.5037    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3821   -0.7736    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9322    4.6152    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5892    3.1497    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5808    3.2803    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9864    0.4115    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2262    2.3919    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2215   -0.2694    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9492   -2.2616    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0029   -4.9909    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0226   -4.8179    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3162   -2.8929    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7586   -4.8142    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1064   -4.7164    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6681   -2.5813    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7912   -4.2301    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3861   -1.5413    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 13  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17  2  1  0
  2  1  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  1
  4  6  1  0
  6  7  1  0
  7  8  1  1
  8  9  1  0
  9 10  2  3
 10 11  1  0
 10 12  1  0
  7 13  1  0
  7 17  1  0
  9  4  1  0
 14 32  1  0
 14 33  1  0
 14 34  1  0
 13 31  1  1
 15 35  1  0
 15 36  1  0
 16 37  1  0
 16 38  1  0
 17 39  1  1
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  5 22  1  0
  8 23  1  0
  8 24  1  0
 11 25  1  0
 11 26  1  0
 11 27  1  0
 12 28  1  0
 12 29  1  0
 12 30  1  0
M  END


  Mrv1652309022204472D          

 17 19  0  0  1  0            999 V2000
    2.1298   -0.7289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7029   -0.0229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8481   -0.0120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4314    0.7424    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3320    0.4298    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0806    1.1080    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6560    1.5226    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9299    2.0534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1990    1.5733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5735    1.8627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2104    1.3383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7092    2.6764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2834    2.0944    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1680    2.9113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0299    1.7259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9158    0.9050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0969    0.7519    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  6  0  0  0
  4  6  1  0  0  0  0
  7  6  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
  7 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 17 16  1  1  0  0  0
  2 17  1  0  0  0  0
  7 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0147227

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1CC[C@H]2C(C)=C[C@]3(O)O[C@@]12CC3=C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O2/c1-9(2)13-8-14-11(4)5-6-12(14)10(3)7-15(13,16)17-14/h7,11-12,16H,5-6,8H2,1-4H3/t11-,12-,14-,15-/m0/s1

> <INCHI_KEY>
ISFMXVMWEWLJGJ-JURCDPSOSA-N

> <FORMULA>
C15H22O2

> <MOLECULAR_WEIGHT>
234.339

> <EXACT_MASS>
234.161979948

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
27.2922920761713

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2S,5S,8S)-2,6-dimethyl-9-(propan-2-ylidene)-11-oxatricyclo[6.2.1.0^{1,5}]undec-6-en-8-ol

> <ALOGPS_LOGP>
2.52

> <JCHEM_LOGP>
3.1425060316666666

> <ALOGPS_LOGS>
-2.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.085590991152895

> <JCHEM_PKA_STRONGEST_BASIC>
-4.435632702004686

> <JCHEM_POLAR_SURFACE_AREA>
29.46

> <JCHEM_REFRACTIVITY>
69.1786

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.71e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,5S,8S)-2,6-dimethyl-9-(propan-2-ylidene)-11-oxatricyclo[6.2.1.0^{1,5}]undec-6-en-8-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       3.976  -1.361   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.179  -0.043   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.583  -0.022   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.805   1.386   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -0.620   0.802   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       2.017   2.068   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       3.091   2.842   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.736   3.833   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.372   2.937   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.071   3.477   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.259   2.498   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.324   4.996   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.262   3.910   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.047   5.434   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.656   3.222   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.443   1.689   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.914   1.404   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   17                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6    9                                             
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   13   17                                             
CONECT    8    7    9                                                       
CONECT    9    8    4   10                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    7   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16    2    7                                                  
MASTER        0    0    0    0    0    0    0    0   17    0   38    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₂O₂

Average Mass

234.3390 Da

Monoisotopic Mass

234.16198 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C[C@H]1CC[C@H]2C(C)=C[C@]3(O)O[C@@]12CC3=C(C)C

InChI Identifier

InChI=1S/C15H22O2/c1-9(2)13-8-14-11(4)5-6-12(14)10(3)7-15(13,16)17-14/h7,11-12,16H,5-6,8H2,1-4H3/t11-,12-,14-,15-/m0/s1

InChI Key

ISFMXVMWEWLJGJ-JURCDPSOSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Curcuma phaeocaulis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as guaianes. These are sesquiterpenoids with a structure based on the guaiane skeleton. Guaiane is a bicyclic compound consisting of a decahydroazulene moiety, substituted with two methyl groups and a 1-methylethyl group at the 1-, 4-, and 7-position, respectively.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Guaianes

Alternative Parents

Substituents

Guaiane sesquiterpenoid
Pyran
Oxolane
Hemiacetal
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.52	ALOGPS
logS	-2.8	ALOGPS

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00020351

Chemspider ID

30845906

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12304275

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Fei C, Ji D, Tong H, Li Y, Su L, Qin Y, Bian Z, Zhang W, Mao C, Li L, Lu T: Therapeutic mechanism of Curcuma aromatica Salisb. rhizome against coronary heart disease based on integrated network pharmacology, pharmacological evaluation and lipidomics. Front Pharmacol. 2022 Aug 9;13:950749. doi: 10.3389/fphar.2022.950749. eCollection 2022. [PubMed:36016561 ]
Yang X, Li B, Tian H, Cheng X, Zhou T, Zhao J: Curcumenol Mitigates the Inflammation and Ameliorates the Catabolism Status of the Intervertebral Discs In Vivo and In Vitro via Inhibiting the TNFalpha/NFkappaB Pathway. Front Pharmacol. 2022 Jun 20;13:905966. doi: 10.3389/fphar.2022.905966. eCollection 2022. [PubMed:35795557 ]
Mao Z, Zhong L, Zhuang X, Liu H, Peng Y: Curcumenol Targeting YWHAG Inhibits the Pentose Phosphate Pathway and Enhances Antitumor Effects of Cisplatin. Evid Based Complement Alternat Med. 2022 Jun 26;2022:3988916. doi: 10.1155/2022/3988916. eCollection 2022. [PubMed:35795276 ]
Wang M, Yu MT, Peng MM, Yin ZZ, Mao CQ, Su LL, Ji D, Lu TL: [Quality evaluation of Curcumae Radix from different origins based on UPLC characteristic chromatogram, multicomponent content, and chemometrics]. Zhongguo Zhong Yao Za Zhi. 2022 Jun;47(11):2964-2974. doi: 10.19540/j.cnki.cjcmm.20210823.301. [PubMed:35718518 ]
LOTUS database [Link]

Showing NP-Card for (1s,2s,5s,8s)-2,6-dimethyl-9-(propan-2-ylidene)-11-oxatricyclo[6.2.1.0¹,⁵]undec-6-en-8-ol (NP0147227)

MOL for NP0147227 ((1s,2s,5s,8s)-2,6-dimethyl-9-(propan-2-ylidene)-11-oxatricyclo[6.2.1.0¹,⁵]undec-6-en-8-ol)

3D MOL for NP0147227 ((1s,2s,5s,8s)-2,6-dimethyl-9-(propan-2-ylidene)-11-oxatricyclo[6.2.1.0¹,⁵]undec-6-en-8-ol)

3D SDF for NP0147227 ((1s,2s,5s,8s)-2,6-dimethyl-9-(propan-2-ylidene)-11-oxatricyclo[6.2.1.0¹,⁵]undec-6-en-8-ol)

3D-SDF for NP0147227 ((1s,2s,5s,8s)-2,6-dimethyl-9-(propan-2-ylidene)-11-oxatricyclo[6.2.1.0¹,⁵]undec-6-en-8-ol)

PDB for NP0147227 ((1s,2s,5s,8s)-2,6-dimethyl-9-(propan-2-ylidene)-11-oxatricyclo[6.2.1.0¹,⁵]undec-6-en-8-ol)

3D PDB for NP0147227 ((1s,2s,5s,8s)-2,6-dimethyl-9-(propan-2-ylidene)-11-oxatricyclo[6.2.1.0¹,⁵]undec-6-en-8-ol)

SMILES for NP0147227 ((1s,2s,5s,8s)-2,6-dimethyl-9-(propan-2-ylidene)-11-oxatricyclo[6.2.1.0¹,⁵]undec-6-en-8-ol)

INCHI for NP0147227 ((1s,2s,5s,8s)-2,6-dimethyl-9-(propan-2-ylidene)-11-oxatricyclo[6.2.1.0¹,⁵]undec-6-en-8-ol)

Structure for NP0147227 ((1s,2s,5s,8s)-2,6-dimethyl-9-(propan-2-ylidene)-11-oxatricyclo[6.2.1.0¹,⁵]undec-6-en-8-ol)

3D Structure for NP0147227 ((1s,2s,5s,8s)-2,6-dimethyl-9-(propan-2-ylidene)-11-oxatricyclo[6.2.1.0¹,⁵]undec-6-en-8-ol)