Levoverbenone

HCID 92874
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Substructure searchFind similar structures

Basic information

CAS
1196-01-6
Standard SMILES
CC1=CC(=O)[C@H]2C[C@@H]1C2(C)C
InChIKey
DCSCXTJOXBUFGB-JGVFFNPUSA-N
Molecular formula
C10H14O
Average molar mass
150.22 g/mol
Monoisotopic mass
150.10446507

Names & identifiers

Preferred name
Levoverbenone
IUPAC
(1S,5S)-4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-one
English name
(-)-Verbenone
Molecular formula
C10H14O
Molecular weight
150.22

Names & synonyms

(-)-Verbenone1196-01-6Levoverbenone(1S)-(-)-Verbenonel-VerbenonePin-2-en-4-one(S)-verbenoneLaevo-verbenoneBicyclo[3.1.1]hept-3-en-2-one, 4,6,6-trimethyl-, (1S,5S)-Verbenone, (-)-Verbenone, (1s)-DTXSID9035620
Show more names
VERBENONEBicyclo[3.1.1]hept-3-en-2-one, 4,6,6-trimethyl-, (1S)-1-VERBENONEVerbenone,(l)[S]-VERBENONE(S)-Verbanone
NSC-6831(1S)-(-)-cis-VerbenoneL(-)-VerbenoneUNII-2XP0J7754U(S)-(-)-Verbenone2XP0J7754UEINECS 214-807-2AI3-23128

Database identifiers

CAS
1196-01-6、80-57-9
PubChem CID
92874
DTXSID
DTXSID9035620
ChEMBL
CHEMBL2426701
ChEBI
CHEBI:78316
UNII
2XP0J7754U
EC Number
201-292-4、214-807-2
Nikkaji
J37.659K

Properties

Computed structural properties

XLogP
1.6
Topological polar surface area
17.1 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
1
Rotatable bonds
0
Heavy atoms
11

Experimental & physicochemical properties

Density0.975-0.981
Solubility · 2 items

Practically insoluble to insoluble in water; soluble in non-polar solvents

Soluble (in ethanol)

Boiling Point89-90 °C (12 mm Hg)
Refractive Index1.490-1.500
Physical DescriptionColourless liquid; Minty spicy aroma

Physicochemical properties

Boiling point
227 · 227-228 °C (lit.)
Density
0.975 g/mL · 0.975 g/mL at 20 °C (lit.)
refractive index
20 · n20/D 1.496(lit.)
FEMA
4216 · 4216 | VERBENONE
Flash point
185 °F · 185 °F
storage temp.
2 · 2-8°C

Safety & regulation

GHS classification

GHS Classification · 6 items

This chemical does not meet GHS hazard criteria for 69.8% (90 of 129) of all reports.

Warning

H302 (30.2%): Harmful if swallowed [Warning Acute toxicity, oral]；H317 (29.5%): May cause an allergic skin reaction [Warning Sensitization, Skin]

P261, P264, P270, P272, P280, P301+P317, P302+P352, P321, P330, P333+P317, P362+P364, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 129 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.；Reported as not meeting GHS hazard criteria per 90 of 129 reports by companies.；There are 2 notifications provided by 39 of 129 reports by companies with hazard statement code(s).；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Hazard information

Regulatory InformationCommission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)
Hazard Classes and Categories · 2 items

Acute Tox. 4 (13.5%)；Skin Irrit. 2 (12.5%)；Skin Sens. 1 (12.5%)；Eye Irrit. 2 (12.5%)；Acute Tox. 4 (12.5%)

Acute Tox. 4 (30.2%)；Skin Sens. 1 (29.5%)

Regulatory information

Regulatory InformationCommission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)

Safety data

F
10
PPE
Eyeshields, Gloves, type ABEK (EN14387) respirator filter
wgk
3
tsca
TSCA listed
ridadr
NA 1993 / PGIII
hs_code
29142900

Chemistry & industry

Pharmacology

ATC Code · 2 items

R - Respiratory system；R05 - Cough and cold preparations；R05C - Expectorants, excl. combinations with cough suppressants；R05CA - Expectorants；R05CA11 - Levoverbenone

QR - Respiratory system；QR05 - Cough and cold preparations；QR05C - Expectorants, excl. combinations with cough suppressants；QR05CA - Expectorants；QR05CA11 - Levoverbenone

Uses & manufacturing

Use Classification · 3 items

Fragrance Ingredients

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

General Manufacturing InformationBicyclo[3.1.1]hept-3-en-2-one, 4,6,6-trimethyl-, (1S,5S)-: ACTIVE
Applications · 2 items

Uses(-)-Verbenone is used to study antioxidant activity of essential oil components in lipid model systems.

General Description(1S)-(-)-Verbenone is one of the main components of the essential oil of Suregada zanzibariensis leaves. It can be prepared by the biotransformation of (-)-α-pinene. (1S)-(-)-Verbenone acts as an antiaggregation pheromone towards the aggregation pheromone released by western pine beetle (WPB).

Upstream & downstream products

Suppliers99 total

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
南京世洲生物科技有限公司025-85560043 15850508050 · [email protected]
湖南韵邦生物科技股份有限公司85561037 15386497078 · [email protected]
成都超九八生物科技有限公司13348960310 13348960310 · [email protected]
上海麦克林生化科技股份有限公司021-50706066 15221275939 · [email protected]

Additional notes

DefinitionChEBI: A 4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-one in which both chiral centres have S configuration.

Related reactions

1 records
New reaction record

Compound notes

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