(-)-alpha-Himachalene

Base Information

• Chemical Name: (-)-alpha-Himachalene
• CAS No.: 3853-83-6
• Molecular Formula: C15H24
• Molecular Weight: 204.356
• UNII: 1DB5J66V5P
• ChEMBL ID: CHEMBL3120652
• DSSTox Substance ID: DTXSID30191859
• Metabolomics Workbench ID: 28349
• Nikkaji Number: J14.594G
• Wikidata: Q27121538
• Mol file: 3853-83-6.mol

Synonyms:(-)-alpha-Himachalene;alpha-Himachalene;3853-83-6;alpha-cis-Himachalene;alpha-Himachalene, (-)-;UNII-1DB5J66V5P;1DB5J66V5P;CHEBI:49218;(-)-2,7(14)-himachaladiene;(4aS,9aR)-3,5,5-trimethyl-9-methylidene-2,4a,6,7,8,9a-hexahydro-1H-benzo[7]annulene;1H-Benzocycloheptene, 2,4a,5,6,7,8,9,9a-octahydro-3,5,5-trimethyl-9-methylene-, (4aS,9ar)-;1H-Benzocycloheptene, 2,4a,5,6,7,8,9,9a-octahydro-3,5,5-trimethyl-9-methylene-, (4aS-cis)-;.alpha.-Himachalene;himachal-4,11-diene;(1R,6S)-alpha-himachalene;.ALPHA.-CIS-HIMACHALENE;CHEMBL3120652;DTXSID30191859;(-)-.ALPHA.-HIMACHALENE;.ALPHA.-HIMACHALENE, (-)-;LMPR0103480001;Q27121538;(4aS,9aR)-3,5,5-trimethyl-9-methylene-2,4a,5,6,7,8,9,9a-octahydro-1H-benzo[7]annulene;(4aS,9aR)-3,5,5-trimethyl-9-methylidene-2,4a,5,6,7,8,9,9a-octahydro-1H-benzo[7]annulene

Chemical Property of (-)-alpha-Himachalene

Chemical Property:

• Vapor Pressure: 0.013mmHg at 25°C
• Boiling Point: 268.359°C at 760 mmHg
• Flash Point: 104.917°C
• PSA: 0.00000
• Density: 0.894g/cm³
• LogP: 4.72520
• XLogP3: 4.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 204.187800766
• Heavy Atom Count: 15
• Complexity: 293

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=CC2C(CC1)C(=C)CCCC2(C)C
• Isomeric SMILES: CC1=C[C@H]2[C@@H](CC1)C(=C)CCCC2(C)C

Technology Process of (-)-alpha-Himachalene

There total 3 articles about (-)-alpha-Himachalene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

(2-cis,6-trans)-farnesyl diphosphate (40716-68-5) → β-himachalene (1461-03-6) + α-himachalene (3853-83-6) + 2-himachalen-7-ol (1891-45-8) + α-ylangene (947-59-1,3856-25-5,13567-62-9,14912-44-8,15493-66-0,15917-91-6,138874-68-7) + γ-cis-himachalane (53111-25-4) + humula-4,9-dien-8-ol + isobicyclogermacrene + γ-humulene + δ–amorphene + α-Amorphene

Guidance literature:

With Medicago truncatula multiproduct sesquiterpene synthase; In pentane; at 30 ℃; for 1.5h; pH=7.5; stereospecific reaction; Enzymatic reaction;

DOI:10.1021/acs.joc.6b02696

Reference yield:

(+)-α-Longipinene (5989-08-2) → β-himachalene (1461-03-6) + α-himachalene (3853-83-6) + longifolene (475-20-7) + (-)-isolongifolene (1135-66-6)

Guidance literature:

With boron trifluoride diethyl etherate; In diethyl ether; at 18 - 29 ℃; for 7h;

DOI:10.1016/S0040-4020(01)81583-0

Reference yield:

humula-4,9-dien-8-ol (116538-30-8) → γ-humulene (26259-79-0) + α-himachalene (3853-83-6) + 2,4a,5,6,7,8-hexahydro-3,5,5,9-tetramethyl-1H-benzocycloheptene (1461-03-6,66141-06-8,94297-35-5,17928-54-0)

Guidance literature:

With pyridine; trichlorophosphate; at 0 ℃; for 14h; Title compound not separated from byproducts;

DOI:10.1007/BF00633390

upstream raw materials:

(+)-α-Longipinene

humula-4,9-dien-8-ol

(2-cis,6-trans)-farnesyl diphosphate

Downstream raw materials:

(S)-1,1,5,8-tetramethyl-1,2,3,4,5-pentahydrobenzo[a][7]annulene

Refernces

• 1、 Shastri, Mayank H.,Dev, Sukh. "Studies in sesquiterpenes-lx reversion of longipinane to himachalane system: Revision of structure of isocentdarol". . p. 4905 - 4918. Retrieved 2007/10/02.